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Practice Tests, Organic Chemistry I Table of Contents

Online Organic Chemistry I, Chem 350, Dr. Craig P. Jasperse, Minnesota State University Moorhead
For full class website, see
https://collaborate.mnstate.edu/public/blogs/jasperse/online-organic-chemistry-courses/online-organic-chemistry-i-350-fall-spring/

Test Page
Test 1 Version 1 3
Test 1 Version 2 9
Test 1 Version 3 15
Test 1 Version 4 21

Test 2 Version 1 27
Test 2 Version 2 33
Test 2 Version 3 39
Test 2 Version 4 43

Test 3 Version 1 49
Test 3 Version 2 55
Test 3 Version 3 61
Test 3 Version 4 67

Test 4 Version 1 73
Test 4 Version 2 79
Test 4 Version 3 85

Final Exam Version 1 93

Final Exam Version 2 101
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JASPERSE CHEM 350 TEST 1 VERSION 1 Organic Chemistry I - Jasperse

Intro and Review
Structure and Properties of Organic Molecules
Structure, Nomenclature, and Conformation/Stereochemistry of Alkanes

1. Draw the correct Lewis structure of CH3CN. (Needn’t show 3-D geometry) (3pt)

2. Draw the correct Lewis structure for HOCH2CHO. (Needn’t show 3-D geometry). (3pt)

3. Draw a 3-dimensional picture for the atoms in CH3CO2CH2NHCH3, using the hash-wedge
convention. (You needn’t specify lone pairs, and orbitals need not be shown). (5pt)

4. For the structure shown, what is the hybridization, electron-pair geometry, and approximate
bond angle (90, 109, 120, or 180) relative to: (6pt)
1 3 4 7
5 6 N
HO 2 +
8

O H
9
electron-pair bond electron-pair bond
hybridization geometry angle hybridization geometry angle

O-1 C-5

C-2 N-7

C-3 O-9

5. Assign any formal charges to any apropriate atoms for proline, given the structure shown (one
of the body’s 20 monomers from which protein and enzyme biopolymers are constructred). (3pt)

O
O
NH 2

1
 4
2

6. Rank the acidity of the following, from 1 (most) to 4 (least). (4pt)

OH OH
N
O H

7. Which of the following represent pairs of resonance structures? (4pt)

a.

b.

OCH 3 OCH 3
c.
Br Br

d. Both a and c

e. a, b, and c are all resonance structures.

8. Draw arrows to show electron-movement in the following two steps (draw arrows for each
step). Draw a circle around the atom that functions as nucleophile in step 1, and a square around
the atom that functions as nucleophile in step 2. (5pt)

Br Step 1 Br
O O Step 2 O + Br
+ OH

OH OH
(anion)

9. Rank the series on the basis of boiling point, 1 having highest boiling point, 3 having lowest.
(3pt)
O
OH

10. Rank the series on the basis of water solubility, 1 having highest solubility, 3 having lowest.
(3pt)
OH OH

2
 5
3

11. For each of the following pairs of resonance structures, circle the one that would make a
greater contribution to the actual resonance hybrid. (4pt)

O O

OCH3 OCH3
(anions)

12. Cyclopropane is much more “strained” than cyclopentane. Why? (Short!) (3pt)

13. For the following acid-base reaction,

a. put a box around the weakest base in the reaction
b. put a circle around the weakest acid
c. draw an arrow to show whether the equilbrium goes to the right or left. (4pt)

O O
+ H 2O + NaOH
ONa OH

14. Classify the relationship between the pairs of molecules as either: (8pt)
same compound structural isomers resonance structures
geometric isomers not isomers (different molecular formulas)

OH OH

CH3 CH3
H CH3 H H Br
Br H
OH H
H H H H CH3H H H OH

3
 6
4

15. Give the name for the following. (7pt)

H
H CH3

16. Identify all the funtional groups in the following molecules. (Do not include “alkane”, since
that isn’t “functional”.) (6pt)

O N O O
O O H

17. Which of the following pair will have the larger rotation barrier, relative to the bonds
indicated? (3pt)

18. For the following Newman projections, rank them in stability from 1 to 4, 1 being most
stable. Identify the “anti” conformation, the “gauche” conformation, and the “totally eclipsed”
conformation. (6pt)
CH3 CH3 H3CCH H3C
3 H
H CH3 H H

H H3C HH
H H H H CH3H H HH H

19. Draw the Newman projection for the most stable conformation of 1,2-dichloroethane. (3pt)

4
 7
5

20. Draw the two chair conformations of cis-1-ethyl-4-methylcyclohexane. (You don’t have to
draw all the hydrogens). (5pt)

21. Which is more stable, cis- or trans-1-t-butyl-2-methylcyclohexane? Draw the best

conformation of the more stable isomer. (4pt)

22. Draw as many structural isomers as you can for C6H14. Be careful not to draw the same
isomer twice! I will take off points for duplicating! (6pt)

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JASPERSE CHEM 350 TEST 1 VERSION 2 Organic Chemistry I - Jasperse

Intro and Review
Structure and Properties of Organic Molecules
Structure, Nomenclature, and Conformation/Stereochemistry of Alkanes

1. Draw the correct Lewis structure of CH3CO2CH2COCH3. (Needn’t show 3-D geometry) (3pt)

2. Draw a 3-dimensional picture for the atoms in CH3CH2CHCHCH2NHCH2CHO, using the hash-
wedge convention. (You needn’t specify lone pairs, and orbitals need not be shown). (5pt)

3. For the structure shown, what is the hybridization, electron-pair geometry, and approximate bond
angle (90, 109, 120, or 180) relative to: (7pt, 2 points off for each error)

O
5
1 3 4 N
6
O H
2

electron-pair bond electron-pair bond

hybridization geometry angle hybridization geometry angle

C-1 C-4

O-2 N-5

C-3 C-6

4. Assign any formal charges to any appropriate atoms for the structure shown below. (4pt)

HO O
N CH 3
CH 3
 10
2

5. Rank the acidity of the following, from 1 (most) to 4 (least). (4pt)

HO OH NH 2
O

6. For the following pairs, identify as “isomers” (“I”) or “resonance structures” (“R”). (6pt)

O O
OH
OH

7. Draw arrows to show electron-movement in the following reactions. (These are reactions, not
resonance.) (5pt)

H
O O H
+ Br + Br O H O O
a. + HO

b.

8. Rank the series on the basis of boiling point, 1 having highest boiling point, 3 having lowest. (3pt)

NH 2 NH 2

9. Rank the series on the basis of water solubility, 1 having highest solubility, 3 having lowest. (3pt)

OH OH
 11
3

10. Circle whichever of the following could fit the formula C5H10? (3pt)

11. For the following acid-base reaction,

a. put a box around the weakest base in the reaction
b. put a circle around the weakest acid
c. draw an arrow to show whether the equilibrium goes to the right or left. (4pt)

OH + NHNa ONa + NH 2
O O

12. Classify the relationship between each pair of molecules as either: (10 pt)
same compound structural isomers resonance structures
stereoisomers

H 3CO H 3CO

iPr iPr H H
Br Br
H H H H
H
H CH 3 H N
CH 3 H H Br HN
CH2CH 3 Br H
 4 12

14. Give the name for the following. (7pt)

H H

15.
16. Identify and write down the names for each of the functional groups in each of the following
molecules. (Do not include “alkane”, since that isn’t “functional”.) For each molecule, try to write
the names in order, as they appear from left-to-right in the molecules. (8pt)
O OH O O
O
H NH 2
O NH

17. Circle which of the following pair will have the larger rotation barrier, relative to the bonds
indicated? (2pt) Identify which reason explains why: steric strain, torsional strain, or angle strain?

18. For the following Newman projections: (6pt total)

a. rank them in stability from 1 to 4, 1 being most stable
b. identify the “anti”, “gauche”, and the “totally eclipsed” conformations.
CH 3 H
H H H H
H H H H H H
H H 3C

H H H 3C H
CH 3 H
CH2CH 3 H 3CH2C CH2CH 3 H 3CH2C

c. Is the energy difference between the gauche and the anti conformation based on steric strain,
torsional strain, or angle strain?

d. In the case of ethane (not shown), staggered conformations are better than eclipsed
conformations. Is the difference based on steric strain, torsional strain, or angle strain?

19. Draw both the most stable and the least stable Newman projections for 1-bromopropane,
BrCH2CH2CH3, relative to C1-C2 bond. - (3pt)
 13
5

20. Which of the following are correct Lewis structures, including formal charges, for nitric acid,
HNO3. (3 pts)
O O O
H N O
H O N O H O N O
O
A B C
21.
a. A only
b. B only
c. C only
d. Both A and C
e. All of the above

22. Draw the two chair conformations of cis-1-isopropyl-4-methylcyclohexane. (You don’t have to
draw all the hydrogens). (5pt) (Use “iPr” as abbreviation).

23. Draw the best chair conformation of the more stable isomer. Which is more stable, cis- or trans-1-
butyl-2-methylcyclohexane? (4pt)

24. Draw any 6 of the 9 possible structural isomers for alkanes with formula C7H16. When deciding
whether to draw cyclic or acyclic alkanes, make sure that you fit the formula! Be careful not to
draw the same isomer twice! I will take off points for duplicating! (You can try to show off by
getting more than 6, but if you do still be sure you don’t duplicate!) (6pt)
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JASPERSE CHEM 350 TEST 1 VERSION 3 Organic Chemistry I - Jasperse

Intro and Review
Structure and Properties of Organic Molecules
Structure, Nomenclature, and Conformation/Stereochemistry of Alkanes

1. (12 points) Give the relationship between the following pairs of structures. The possible
relationships are the following:
same compound structural isomers resonance structures
stereo isomers not isomers (different molecular formula)

H H
Br Br
a.
Br
H
Br H

H Br H H
b. H C C H H C C H
Br H Br Br

c. Br Br

d.

e.

f.

2. (8 points) Draw line-angle structures and names for 4 of the 5 structural isomers of C6H14.

1
 2 16

O
OH
H 2N 2
3
4
5
6
7 8
3. (10 Points) 1

a. For the above structure, what is the hybridization and approximate bond angles (109, 120, or
180) about:

C-2

C-4

C-6

O-8

b. In the above structure, N-1 is actually found to have 120º bond angles. (This may seem
unexpected to you at this point, but we’ll learn why later in the course.) What must be the
hybridization of the nitrogen?

4. (2 Points) Bond rotation around C6-C7 in the above structure has a 7 kcal/mol barrier, while
rotation around the C4-C5 bond has a 70 kcal/mol barrier. Explain very briefly why it is so
much harder to rotate the latter bond?

5. (4 points) For each of the pairs listed, circle the one with the higher boiling point.

CH3 H
a. N N

b. OH OH

6. (6 points) Write a Lewis structure and assign any non-zero formal charges.

a. [CH3NH3]+

b. CH3CO2Na

c. CH3CHO

2
 3 17

7. (5 points) a) Draw the best resonance structure for anion A, and circle the resonance
structure that would make the greater contribution to the resonance hybrid.

O
N
A

b. For the two resonance structures shown below, circle the resonance structure that would make
the greater contribution to the resonance hybrid.
+ NH
2 NH2
+

8. (6 points) Rank the acidity of the following molecules, 1 being most acidic, 4 being least
acidic. Hint: draw the anions!

NH3 CH3CH2OH CH3CO2H HCl

9. (6 points) Draw a line-angle picture for all of the atoms in the molecule
CH3CH2COCHClCH3, including the hydrogens. Use the hash-wedge convention to indicate
atoms that are not in the plane of the paper.

10. (5 points) Rank the ring strain in the following, from 1(most) to 3 (least). Explain very
briefly the differences in strain.

A
B C

3
 4 18

11. (6 points) Which of the following are capable of cis-trans stereoisomerism? (Yes/No).

a. 3-ethyl-1,1-dimethylcyclopentane

b. 3-pentene (name means a double bond is between carbons 3 and 4)

c. 1,3-dimethylcyclohexane

12. (9 points) Identify the functional groups in the following molecules. (Do not include
"alkane", since that is not "functional". And do not specify "cyclic".)

a. H 2N CO 2H
("GABA: brain neurotransmitter")

OH
CH 3
H
CH 3 H

b. H H
O
Testosterone

CH 3 O O
CH 3
N
H
c.
O
H
Cocaine O

4
 5 19

13. (5 points) Give the IUPAC name for the following compounds.

H
CH 3
a. b.
H
CH 2CH 2CH 3

14. (8 points) a. Draw Newman projections for the totally eclipsed, the gauch, and the anti
conformations of 2,5-dimethylhexane, relative to the C3-C4 bond. You may abbreviate the
isopropyl groups attached to C3 and C4 as "i-Pr" for convenience.
b. Explain very briefly why the rotation barrier around the C3-C4 bond of 2,5-dimethylhexane is
greater than the rotation barrier in butane.
4 4
= i-Pr
3 3 i-Pr

15. (8 points) a.) Draw the two chair conformations of cis-3-methyl-1-isopropylcyclohexane.

(You don't need to show the H's on carbons other than 1 and 3). For convenience, you may
abbreviate methyl as "Me" and isopropyl as "iPr"
b.) Circle the more stable conformation.
c) Would trans-3-methyl-1-isopropylcyclohexane be more stable or less stable than the cis
isomer?

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JASPERSE CHEM 350 TEST 1 VERSION 4 Organic Chemistry I - Jasperse

Intro and Review
Structure and Properties of Organic Molecules
Structure, Nomenclature, and Conformation/Stereochemistry of Alkanes

1. Order the following according to increasing electronegativity, 1 being highest, 4 lowest. (2pts)

N F O C

2. Write Lewis structures and assign any non-zero formal charges. (3pts each)

a. [CH3OH2]+

b. CH3CO2CH2ONa

c. CH3CHCHCONH2

3. For each of the following, a) draw its resonance structure, and for each pair b) circle the
structure that would make the greater contribution to the resonance hybrid. (2 pts each)

O
a.

H
b.
O+

4. Draw line-angle structures for 7 of the 9 structural isomers of C7H16. (5 pts)

 2 22

5. For the following pairs of structures, identify them as either: Resonance Structures, Structural
Isomers, Stereoisomers, or Same. (2 pts each)

OH O
a.

H H H CH 3
b.
H 3C CH 3 H 3C H

c.

d.

e. CH3CH2CH2CH2CH3 (CH3)2CHCH2CH3

6. Rank the acidity of the following molecules, 1 being most acidic, 4 being least acidic. (3 pts)

CH3NH2 CH3OH HCO2H CH3CH3

O O
+ CH 3 + CH4
7.

a) Put a box around the weakest base in the above reaction. (1pt)
b) Put a circle around the weakest acid in the above reaction. (1pt)
c) Draw an arrow to show whether at equilibrium the reaction will go left-to-right or right-to-
left. (2pt)
 3 23

8. Draw the line-angle structure for the following condensed structural formula: (CH3CH2)2CO
(3pt)

9
H 2N 2
3
4
5
6
7
8
9. 1
a. For the above structure, what is the hybridization, electron-pair geometry, and approximate
bond angles (109, 120, or 180) about: (6pt)

N-1

C-3

C-5

C-8

b. Rank the length of the following bonds, 1 being shortest, 3 being longest. (2pt)

C2-C3 C4-C5 C8-C9

10. For each of the pairs listed, circle the one with the higher boiling point. (4pt)

a. O
OH

b.

c. O

11. Draw a 3-dimensional picture for all of the atoms (hydrogens included) in the molecule
CH3CHCHCOCH2CH2NHCH3. Your picture should use the hash-wedge convention to
illustrate atoms that are not in the plane of the paper, and should reflect approximate bond
angles. (5pt)
 4 24

12. Draw a 3-D picture of CH2O showing the π bond as well as the four atoms. (3pt)

13. For the following set, rank the solubility in water, from 1 (most soluble) to 4 (least soluble).
(3pt)

OH OH
O

14. Identify the functional groups in the following molecules. (8pt)

O
a. O

O
b.
HO N OH
H

15. Give the IUPAC name for the following compounds. (6pt)

a.

CH 3 H
b.
H CH 3
 5 25

16. Draw the Newman projections for the best and worst conformations of butane, and give the
names for these conformations. Briefly explain what “strain factors” make the worst
conformation worse than the best conformation. (6pt)

17. a.) Draw both chair conformations of cis-1-methyl-2-isopropylcyclohexane. Draw the

substituents and H-atoms attached to carbons 1 and 2. (You don't need to show the H's on the
other carbons). (4pt)
b.) Circle the more stable conformation. (1pt)

18. Draw the best chair conformation for 1,3-diethylcyclohexane, and identify whether it is “cis” or
“trans”. (3pt)

19. Use the arrow-pushing convention to show the electron-movement mechanisms for the follow
two reactions. (5pt)

OH2
O O
a. + CH 3 b. + OH2
NH 2 NH 2
CH 3
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JASPERSE CHEM 350 TEST 2 VERSION 1
Ch. 4 The Study of Chemical Reactions; Ch. 5 Stereochemistry
Ch. 6 Alkyl Halides: Nucleophilic Substitution and Elimination

1. Predict the major organic product for each of the following. (3 points each)

Br2, hv

CH3SNa
Br

I
NaOCH2CH3

2. Show an alkyl bromide and some nucleophile that you could use to make the following by
SN2. (3 points)

OCH2CH 3

3. For the structure shown, (3 points each)

a. Draw the major elimination product
formed upon treatment with H2O/heat.

D H
Br
H CH3
H

b. Draw the major elimination product

formed upon treatment with CH3CH2ONa.

c. Draw the major substitution product

formed upon treatment with CH3CH2ONa.
 28
(3 points for each multiple choice question)
4. Which of the following is true regarding an SN1 reaction?
a. It would be faster at 25˚ than 50˚
b. It would be faster in ethanol than in pentane
c. Keeping the moles of reactants constant but doubling the quantity of solvent would
decrease the rate by a factor of 4.
d. Stereochemical inversion occurs exclusively

6. Which of the following statements is true?

a. The rate determining step is always the last step in a reaction mechanism.
b. The stability/reactivity principle says that the more stable of two chemicals will be more
reactive
c. The reactivity/selectivity principle says that the more reactive of two chemicals will be less
selective.
d. The activation barrier for a reaction is the difference in energy between reactants and final
products.

7. Which of the following statements is true about the chlorination of methane?

a. In each propagation step a radical is produced
b. 6.02 x 1023 initiation events are needed to make one mole of chloromethane
c. Most chloromethane is made by combination of a methyl radical with a chlorine radical
d. The overall chlorination of methane is strongly endothermic.

8. Which of the following statements is FALSE?

a. Optically active solutions solutions always contain chiral molecules.
b. Two diastereomers always have identical melting points
c. Optically inactive solutions are either racemic or else contain no chiral chemicals at all
d. A solution with 60% optical purity would have an 80/20 mix of enantiomers

9. When the reactants shown undergo substitution, which of the products A-D will form? (3
points)
D H D H D H D OH D CH3
Br H2O OH H H H
???
H CH3 heat H CH3 H CH3 H CH3 H OH
H H A OH B H C H D

a. A only Carbocation rearrangement is involved in this

b. B only problem. *IF* I didn't really spend time
c. A and B discussing carbocation rearrangements in
d. A, B, and C lecture, then don't bother with this problem.
e. A, B, C, and D
 29
10. Rank the reactivity of the structures shown toward the reactant(s) indicated on the left (1
being most, etc.) (3 points each)

Br Br I
NaOCH2 CH3 Br

Br2/hv

O
CH3Br NHLi OLi OH

Br
H2O, heat, Br
Br
Br

11. Carbocations often rearrange, as shown below. Draw in the hydrogens on the two carbons
involved in the rearrangement, and show formal arrow-pushing to illustrate the transformation.
(3 points)
Carbocation rearrangement is involved in this
problem. *IF* I didn't really spend time
+ discussing carbocation rearrangements in
+
lecture, then don't bother with this problem.

12. Draw the mechanism for the following reaction, propagation steps only. (4 points)

Br2, hv Br
 30
13. Draw (3R,6R)-6-bromo-3-chloro-2-methyloctane (3 points)

14. Name the following: (3 points)

H
Br
(optically
active)
H
Cl

15. Classify each of the chiral carbons in the following structures as R or S (there may be more
than one in a molecule). (10 points)

H H CH3 H Cl
OH
CH3
H Br H

16. a. Classify each pair as diastereomers, enantiomers, or same. (12 points)

b. For the first structure of each pair, circle it if it is not chiral
c. For the first structure of each pair, write “meso” by it if it is meso

H
OH
HO OH
OH H H
H
H Br Br H H Br

H Br

Cl Br Br F

H F Cl H

17a. a) Draw all the unique stereoisomers of 2,3-dichlorobutane. Cross out any duplicates.
b) Identify which is meso. c) Identify a pair that are related as diastereomers. (5 points)
 31
18. Draw the mechanisms for the following reactions, using formal arrow pushing. Note: in
some case hydrogens that are not illustrated will be involved in bond changes. You would do
well to write them in at the beginning. (12 points total, 3/3/6 distribution)

Br NaOH OH

Br
NaOH

Br H2O OH

heat (identify the slow step)

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 33

JASPERSE CHEM 350 TEST 2 VERSION 2

Ch. 4 The Study of Chemical Reactions
Ch. 5 Sterochemistry
Ch. 6 Alkyl Halides: Nucleophilic Substitution and Elimination

1. Rank the reactivity of the following molecules toward Br2/hv. (1 most, 4 least) (3 points)

CH3-CH3

2. Rank the reactivity of the following molecules toward ethanol and AgNO3. (1 most, 4 least)
(3 points)

Br Cl Cl Br

3. Rank the reactivity of the following molecules toward NaOCH3. (1 most, 4 least) (3 points)

Br Br
I Br

4. Rank the reactivity of the following toward 1-iodopropane. (1 most, 4 least) (3 points)

CH3ONa CH3CO2H CH3CO2Na CH3SNa

5. What is the hybridization of a carbocation? (2 points)

 34

6. Predict the major organic product (1 major structure is all that is needed in each case) for each
of the following reactions. (Minor products or inorganic side products need not be drawn.)
(3 points each)

Br + CH3CO2Na

hv
+ Br2

Br H Acetone
+ NaI Solvent

7. Draw the structures for intermediate A and final product B. (4 points)

Br2, hv NaOCH3
A B

8. Draw the product when the following substance undergoes E2 elimination. ("D" is deuterium,
basically just a labelled hydrogen). If the starting material is optically active, will the product by
optically active? (4 points)

H 3C Br
H CH3 NaOCH3
H
D
 35

9. Show an alkyl bromide and some nucleophile that you could use to make the following by SN2.
(3 points each)

CH3
O

H OCH3

10. Draw all possible elimination products that could form from the following reactant. Circle the
one that forms in greatest yield. (5 points)

O
Br

11. Which of the following would not increase the rate of an E1 reaction? (3 points)
a. an increase is temperature
b. an increase in the "activation energy"
c. an increase in the concentration of the alkyl halide
d. an increase in the stability of the carbocation intermediate

12. When comparing the reaction of 2-methylpropane with either Cl2/hv or Br2/hv, which of the
following statements is true? (3 points)
a. bromine is less reactive and more selective
b. chlorine is less reactive and more selective
c. bromine is more reactive and more selective
d. chlorine is more reactive and more selective

13. Which of the following statements is true relative to reactions I-III: (3 points)
I CH4 + Br• → CH3• and HBr
II CH3CH3 + Br• → CH3CH2• + HBr
III CH3CH2CH3 + Br• → (CH3)2CH• + HBr
a. I has the smallest energy of activation and the highest energy transition state
b. II has the smallest energy of activation and I has the lowest energy transition state
c. III has the largest energy of activation and the highest energy transition state
d. III has the smallest energy of activation and the lowest energy transition state
 36

14. Classify each of the chiral carbons in the following structures as (R) or (S). (10 points)

Cl
HO H H CH3
Cl
H
H OH H CH3

15. a. Classify each pair of molecules as diastereomers, enantiomers, or same. (12 points)
b. Circle any molecules that are chiral
c. Write "meso" by any structures that are meso
.
Cl H
Cl
H Cl
H
H
Cl

F CH3 H 3C H
H Cl F Cl

O O

H Cl Cl H H Cl

Cl H

16. Which of the following statements is true? (3 points)

a. All solutions with chiral molecules are optically active
b. All molecules with chiral carbons are chiral
c. A solution that has 50% optical purity has a 50/50 mixture of enantiomers
d. Two enantiomers always have identical boiling points

17. Draw (2R,3S)-2-bromo-3-chlorohexane (3 points)

18. Name the following: (3 points)

Cl
Cl
H
 37

19. a) Draw all unique stereoisomers of 2,4-dibromopentane. Label each with a letter, A, B, etc..
Cross out any duplicates. (8 points)
b) Identify any that are chiral
c) Identify any that are meso

20. a) Draw the mechanism for the following reaction. (Draw the propagation steps only.) (4
points)
b) Is your product chiral, and if so is it optically active? (1 points)

H 3C H Br2, hv H 3C Br

21. a) Draw the mechanism for the following reaction. (4 points)

b) Identify the slow step. (1 point)
Br OCH3
HOCH3
38
 39

JASPERSE CHEM 350 TEST 2 VERSION 3

Ch. 4 The Study of Chemical Reactions
Ch. 5 Sterochemistry
Ch. 6 Alkyl Halides: Nucleophilic Substitution and Elimination

1. /4 6. /9 11. /6 16. /4
2. /4 7. /4 12. Removed 17. /6
3. /4 8. /6 13. /6 18. /16
4. /4 9. /10 14. /6
Total /100
5. /3 10. /6 15. /2

1. List the following radicals in order of increasing stability (from most stable 1 to least stable 4)

2. List the following alkyl halides in order of decreasing reactivity toward SN1/E1 reactions (from
most reactive 1 to least reactive 4).

Br
Br Br

Br

3. List the following alkyl halides in order of decreasing reactivity toward SN2 reactions (from
most reactive 1 to least reactive 4).
Br
Br I
Br

4. Rank the bond strength of the following (from strongest 1 to weakest 4).

H-Br H-Cl H-F H-I

5a. Put a 1 by the reaction for which ∆H˚ = Eact. (Eact = activation energy)
b. Put a 2 by the reaction for which Eact = 0.
c. Put a 3 by the reaction for which Eact > ∆H˚.

Br-Br → Br• + Br•

H3C-H + Br• → H3C• + H-Br
H3C• + •CH3 → H3C-CH3
 40

6. Predict the major organic product for each of the following reactions. (Minor products or
inorganic side products need not be drawn.)

hv
+ Br2

Br + NaOH

Br
+ NaOH

7. Show the Starting Alkyl Bromide which gave the following products.

H2O OH
+
heat

8. Show an alkyl bromide and some nucleophile that you could use to make the following. (I
don't care whether you specify a nucleophile just as the anion Z- or as NaZ with a metal
counterion.)

OH

CN

9. Optically active (R)-2-bromobutane can be converted to 2-butanol under either conditions A or

conditions B. Describe the stereochemistry of the product solutions for the two different
conditions.

OH NaOH H Br H2O, heat OH

(Conditions A) (Conditions B)

Conditions A Conditions B
a. Alcohol is Chiral or Achiral?
b. Optically Active or Not?
c. (R), (S), or both?
d. Reaction occured by Inversion,
Retention, or Racemization?
e. What happens to the rates if you double
the concentrations of all reactants?
 41

10. Draw the major product for the following reaction. Then draw the mechanism for its
formation. (Draw the propagation steps only.) Is your product chiral? (You may need to add
relevant hydrogens.)

hv
+ Br2

11. Draw the major product for the following reaction. Then draw the mechanism for its
formation. (You may need to add relevant hydrogens.)

H 3C Br
+ NaOH

13. Draw the mechanism for the following reaction. (Don't worry about designating stereochem.)
H 3C Br H 3C OH
H2O
+ H-Br
 42

14. Classify each of the chiral carbons in the following structures as (R) or (S).

H
CH3
HO H
H
CH3

15. Draw (R)-2-bromopentane

16. Draw meso-1,3-dichlorocyclopentane, and mark the chiral C's as (R) or (S).

17. Draw all of the different isomers of 2,3-dichlorobutane, identify each as either chiral or meso,
and classify the relationship between each two as enantiotopic or diastereotopic. (You may use
Fischer projections or zig/zag/hash/wedge pictures, as you please. (If two are the same, cross one
of them off your list.)

18. Classify the pairs of molecules as diastereomers, enantiomers, or same. For the first molecule
in each pair, circle it if it is chiral. For the second molecule in each pair, put a * next to each chiral
C.
Br H HO Br
H H
H OH

H Cl Cl H

H CH3 H 3C H

H 3C H 3C
 43
1

JASPERSE CHEM 350 TEST 2 VERSION 4

Ch. 4 The Study of Chemical Reactions
Ch. 5 Alkyl Halides: Nucleophilic Substitution and Elimination
Ch. 6 Stereochemistry

1. Draw the mechanism for the following reaction, and write “slow” next to the rate-
determining step. Be sure to draw all intermediates, and to correctly draw “electron-
movement” arrows or half-arrows. (Show the propagation steps only.) (4 points)

H H hv H Br
+ Br 2 + H-Br

2. Draw the mechanism for the following reaction, and write “slow” above the rate-
determning step. Be sure to draw all intermediates, and to correctly draw “electron-
movement” arrows. (5 points)

Br OCH3
H+ (catalyst)
+ HOCH3 + H-Br
CH3 OH (solvent)
heat

3. Predict the major products for the following reactions. (4 points each)

Br + NaOCH CH3 OH (solvent)

a) 3

hv
+ Br 2
b)
 44
2

Br CH3 OH (solvent)
+ NaOCH 3
c)

hv
+ Br 2
d)

Br + CH SNa
e) 3

4. Draw the substitution products for the following reactions. (Do not draw the
accompnaying elimination products). Include stereochemistry in your answer, and if
two substitution products are formed draw them both. (4 points each)

H2O
+ NaOH
H Cl
a) H 3C H

cat. HCl
+ H2O
H Cl H2O
b) 3C
H CH3

5. Draw the E2 elimination product(s) [do not draw the substitution product(s)]. (4
points each)

H NaOCH3
CH3 CH3 OH
H
Br

6. Of the following alkyl halides, (3 points)

a) Circle the one that would be the most reactive toward SN2 substitution
b) Put a box around the one that would be the least reactive toward SN2 substitution

Cl I
I Br
Cl
 45
3

7. Of the following alkyl halides, (3 points)

c) Circle the one that would be the most reactive toward SN1 substitution
d) Put a box around the one that would be the least reactive toward SN1 substitution

Cl I I
Cl
Br

8. Rank the stability of the following carbocations, from 1 (most stable) to 4 (least
stable) (4 pts)

+ + + +

9. Rank the stability of the following radicals, from 1 (most stable) to 4 (least stable) (4
pts)
•
• • •

10. Classify as R or S (2 pts each)

H Br

a) Cl CH3

Br H

b)

c) H 3C H

d) H CH3
 46
4

11. Provide the structure and the IUPAC name for the following (3 pts each)

a) (R)-3-chloro-2-methylheptane

H
Br
b) CH3

12. Classify the paris of molecules as not isomers, structural isomers, diastereomers,
enantiomers, or identical, and circle any molecules that are achiral. (2 pts each)

Br H Br
H
a) H Cl H Cl

H Br Br H
b) Br H H Br

H Cl H CH3
c) H 3C Br Cl Br

13. For 1,2-dimethylcyclopentane, (8 pts)

a) How many stereocenters are present

b) Draw all the possible stereoisomers, and circle those that are chiral.
 47
5

Each of the following multiple choice problems is worth 3 points.

14. For the reaction shown below, with bond dissociation energies listed below each key
bond, the overall ∆H is:

(CH3) 3C-H + Cl-Cl → (CH3) 3C-Cl + H-Cl

∆H (kcal/mol) 91 58 78 103

a) +58 kcal/mol
b) -32 kcal/mol
c) +32 kcal/mol
d) -57 kcal/mol
e) +181 kcal/mol

15. Which factor would not increase the rate of an E1 reaction:

a) Use of a more polar solvent

b) Use of a 3˚ rather than a 2˚ alkyl halide
c) Doubling the concentration of the base
d) Using iodide rather than bromide as leaving group

16. Consider the SN2 reaction shown below. Assuming no other changes, what effect on
the rate would simultaneously doubling the concentrations of both 1-bromobutane
and KOH have?
CH3CH2CH2CH2Br + KOH → CH3CH2CH2CH2OH + KBr
a) No effect
b) It would double the rate
c) It would triple the rate
d) It would increase the rate by four times
e) It would increase the rate six times

17. Of the SN1/SN2/E1/E2 reactions, rearrangements are likely to occur in:

a) SN1 reactions only

b) SN2 reactions only
c) E1 reactions only
d) Both SN1 and E1 reactions
e) Both SN2 and E2 reactions
48
 1
JASPERSE CHEM 350 TEST 3 VERSION 1
Ch. 7 Structure and Synthesis of Alkenes
Ch. 8 Reactions of Alkenes

1. How many elements of unsaturation are in the formula C6H9NO2? (3 points)

a. 0 b. 1 c. 2 d. 3 e. 4 f. 5 g. 6

2. For the three structures shown, which of the statements is true? (3 points)

NO2
NO2
A B C D

a. A, C, and D are Z; B is E
b. A and B are the only Z compounds
c. A is the only Z compound; B is the only E compound
d. B, C, and D are Z; A is E
e. B is the only Z compound; A is the only E compound

3. Rank the reactivity of the following toward H2SO4/Î catalyzed dehydration. (3 points)
a. A is fastest; C is slowest
b. B is fastest; C is slowest
c. A is fastest; B is slowest
d. C is fastest; B is slowest
e. B is fastest; A is slowest
f. C is fastest; A is slowest

OH HO
OH
A B C

4. Which of the following reactants would give exaactly the same products from both (E)- and
(Z)-2-butene? (3 points)

a. Br2
b. PhCO3H
c. 1) BH3-THF 2) NaOH, H2O2
d. OsO4, H2O2
e. D2, Pt

5. Draw the alkene that gives the product shown, and specify its stereochemistry. (2 points)

OH
OsO4, H2O2

OH
1
 2
6. Draw the major product for each of the following reactions or reaction sequences. You
needn’t bother to show side products or minor products. For chiral molecules that are racemic ,
you needn’t draw both enantiomers. BE CAREFUL TO SHOW THE CORRECT
ORIENTATION, AND THE CORRECT STEREOCHEMISTRY IN CASES WHERE
STEREOCHEM IS FACTOR. (3 points each)

1. Hg(OAc)2, H2O

2. NaBH4

Br
NEt3

OH
H2SO4, heat

H-Br

CH3CO3H

H2O

1. H-Br

2. NaOH

1. NaOCH2CH3 Skip This one. It involves

KMnO4, a reaction I covered in
Br 2. KMnO4, heat years past but not this year.

Br2, H2O

HBr, peroxides

2
 3
7. A single unknown reacts with O3/Me2S to give the following three products. What is the
structure for the unknown? (3 points)

O O O
1. O3
H H + +
2. Me2S
O

8. Provide the name or structure for the following. (3 points each)

Cl

(racemic, don’t do
R/S stuff)

9. Provide a possible structure for a compound with formula C5H8, given that it reacts with
excess H2/Pt to give C5H10. (3 points)

10. Fill in the blanks for the following reaction sequence: (6 points)

Br2, NaOCH3

hv CH3OH
PhCO3H

11. Consider how the Se-O bond would be polarized and predict the product which would result
when CH3SeOH adds to propene: (Selenium is located two rows directly below oxygen on the
periodic table). (3 points)

CH3Se-OH

3
 4
12. When the following isomeric alkenes are fully burned, rank the amount of heat produced in
the combustions, from most heat produced (1) to least heat produced (4). (3 points)

13. Provide structures for starting material A and reactions products B and C, given the formula
of starting material A and the stereochemical status of products B and C. (5 points)

Cl2 A PhCO3H
B C
racemic C 4H 8 meso
mixture compound

14. Draw mechanisms for the following reactions, using formal arrow-pushing. Each
intermediate along the mechanism pathway must be shown. (6 points, 3 points, 6 points)

OH H2SO4

heat

HBr

Br

Br2, H2O HO Br

(be sure your mech. is consistent with

the observed stereochemistry)

4
 5
15. Provide reagents for the following transformations. (5 points each)

Br
OH

OH
OH
O
Skip This one. It involves
KMnO4, a reaction I covered in
years past but not this year.

H3C Br
Br

5
54
 1
JASPERSE CHEM 350 TEST 3 VERSION 2
Ch. 7 Structure and Synthesis of Alkenes
Ch. 8 Reactions of Alkenes

1. How many elements of unsaturation are in the formula C8H9N?

a. 0
b. 1
c. 2
d. 3
e. 4
f. 5

2. Provide the proper IUPAC name for the alkene shown below.
Br

CH 3

3. Provide the proper IUPAC name for the alkene shown below.
ClCH 2CH2 CH 3
C C
H H

4. Draw an acceptable structure for 4-phenyl-1-butene.

5. Draw the alkene of formula C4H8 which evolves the most heat per mole upon hydrogenation

6. Choose the most stable alkene among the following.

a. 1-hexene
b. (E)-2-hexene
c. (Z)-2-hexene
d. They are all of equal stability according to Saytzeff's rule.

1
 2

7. Draw the major product of the following reaction.

Br
+
(CH 3)3CO - K
CH
3 (CH 3)3COH

8. Draw the major product and the mechanism.

CH
3
H 2SO4
OH

heat

9. Which of the following best describes the geometry about the carbon-carbon double bond in the
alkene below?
CH3

Cl

a. E
b. Z
c. Neither E nor Z

10. Draw 3 examples of molecules with the formula C4H6O2.

11. Draw the major product.

H-Br

12. Draw the major product.

1. Hg(OAc)2, CH3OH
2. NaBH4

2
 3

13. Draw the major product.

1. BH3 • THF
2. H2O2, -OH

14. Draw the major product.

CH3 CH3
Cl2, H2O

H H

15. Draw the major product.

CH3
OSO4

H2O2

16. Draw the major product.

CH3 1. O3
2. (CH3)2S

17. Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

H+, H2O

3
 4

18. Suggest a reasonable detailed, step-by-step mechanism for the reaction shown below.

Br
HO Br2 + HBr
O

This one is very hard. It's a

challenge problem. Kind of an
extension using ideas from
class but pushing a little bit
beyond what was covered. Few
students got this one correct.

19. Provide the reagents necessary to complete the following transformation. (2 steps minimum).

OH OH

OH

20. Both (E)- and (Z)-3-hexene can be treated with D2 in the presence of a platinum catalyst. How are
the products from these two reactions related to each other?

a. The (E)- and (Z)-isomers generate the same products in exactly the same amounts.
b. The (E)- and (Z)-isomers generate the same products but in differing amounts.
c. The products of the two isomers are related as diastereomers.
d. The products of the two isomers are related as enantiomers.
e. The products of the two isomers are related as structural isomers.

21. Consider how the I-Cl bond is polarized and predict the product which results when this mixed
halogen adds to 1-methylcyclohexene.

4
 5
22. β-Ocimene is a perfume. Suggest a possible structure for β-ocimene that is consistent with the
following information.

H2,Pt
ß-Ocimene 2,6-dimethyloctane
(C10H16)

1. O3 CH2O + CH3COCH3 + CH3COCHO

2. (CH3)2S + OHCCH2CHO

23. Fill in the starting reactant.

1. BH3-THF H OH

2. NaOH, H2O2 H CH3

24. Fill in the blanks for the following reaction sequence.

1. Hg(OAc)2 , H2 O H2 SO 4,
A B
2. NaBH4 heat

KMnO4
Skip This Last Step.
It involves KMnO4, a reaction I
covered in Cyears past but not
this year.

25. Provide reagents to carry out the following transformation: (3 steps minimum)

Cl

Cl

5
60
JASPERSE CHEM 350 TEST 3 VERSION 3
Ch. 7 Structure and Synthesis of Alkenes
Ch. 8 Reactions of Alkene
The number of points per problem is indicated in parentheses following each problem.

1. Rank the following alkenes in order of stability, 1 being most stable, 4 being least stable. (4)

2. Determine the number of elements of unsaturation for C5H7ClO. (3)

3. Give the proper IUPAC name or the structure for the following compounds. (4 points each)

a. (E)-2-chloro-3-methyl-2-pentene

b.

4. Rank the reactivity of the following alcohols towards HBr, 1 being the fastest reactant, 3
being the slowest reactant. (3 points)

1
5. Predict the major product for the following reactions. You needn't bother to show any side
products or minor products. Pay careful attention to orientation. (3 points each)

H2O, H+

1. Hg(OAc)2, CH3OH

2. NaBH4

potassium

Br tert-butoxide
(KOCMe3)

H2SO4, !

HO

6. Predict the major product in each of the following reactions. Pay careful attention to
stereochemistry! (3 points each)

H2, Pt

Br2

Cl2, H2O

OsO4, H2O2

2
7. Fill in the starting reactant. (4 points each)

CH3CO3H H OH

H2O
H OH

8. Provide the major product of the following reaction sequences. (4 points each)
OH
Î
1. H2SO4, heat

2. Br
22

Br 1. NEt3, heat
2. HBr, peroxides

3. NaOCH3

9. What is a possible structure for a molecule A given the following: (6 points)

a. is has the formula C6H10
b. it reacts with H2/Pt to give a product with formula C6H12
c. upon ozonolysis (O3; Me2S) it gives two products, CH2=O and a product C5H8O.

3
10. Fill in the boxes. (6 points total)

O
Î
KMnO4, heat
OH

O
Ignore this part It involves KMnO4,
a reaction I covered in years past
1. O3 but not this year.
2. Me2S

11. Provide reagents to accomplish the following transformations. (6 points each)

Br

OH

CH3
Br H
OH
H

4
12. Draw the mechanisms for the following reactions. Be sure to draw all intermediates, and try
to correctly draw "electron-movement" arrows. (8 points for the first, 6 points for the second)

OH
H2SO4, Î
heat

HBr Br

CH2 CH3

13. Draw as many isomers as you can for alkenes with formula C5H10. (8 points. 2 points off
for each duplicate or each possible isomer not drawn.)

5
66
JASPERSE CHEM 350 TEST 3 VERSION 4
Ch. 7 Structure and Synthesis of Alkenes
Ch. 8 Reactions of Alkenes

1. Rank the following alkenes in order of stability, 1 being most stable, 4 being least stable. (3
points)

2. Determine the number of elements of unsaturation for C5H8O. (2 points)

3. Give the proper IUPAC name or the structure for the following compounds. (3 points each)

a. 4-vinylcyclopentene

b.

4. Rank the reactivity of the following alcohols towards H2SO4/∆ catalyzed dehydration, 1
being
the fastest reactant, 3 being the slowest reactant. (3 points)
HO CH3 HO H HO CH3

1
5. Which of the following statements is true for the structures shown: (3 points)
a. A is Z and B is Z
b. A is Z and B is E
c. A is E and B is Z
d. A is E and B is E

Cl
A B

OCH3

6. Predict the major product for the following reactions. You needn't bother to show any side
products or minor products. Pay careful attention to orientation, which is important in many of
these problems. (3 points each)

HBr, no peroxides
a.

1. Hg(OAc)2, H2O
b.
2. NaBH4

H2, Pt
c.

d. PhCO3H

Br NaOCH3
e.

Br
potassium
t-butoxide
f.
(KOCMe3)

2
7. Predict the major product in each of the following reactions. Pay careful attention to
stereochemistry: stereochemistry is involved in each of these problems! (3 points each)

a. Br2, H2O

b. OsO4

H2O2

1. BH3-THF
c.

2. H2O2, NaOH

CH3CO3H, H 2O
d.

8. Fill in the intermediates in the following transformation. (3 points each)

H2SO4, ! HBr,

OH Peroxides
A B
Î
NEt3, heat

OMe 1. Hg(OAc)2, MeOH

2. NaBH4
C

3
9. For the following reactions, fill in the missing starting materials, reagents, or products. (3
points each)

Br2 H Br
a.

H Br

b. OH

O Me O
1. O3
c.
Me H
2. Me2S

Î
KMnO4, heat
Skip This one. It involves
KMnO4, a reaction I covered
in years past but not this year.

d.

4
10. Provide the major product of the following reaction sequences. (4 points each)
1. H2O, H+

2. H2SO4, !

1. HBr, peroxides

2. KOCMe3
3. Br 2

11. Provide reagents to accomplish the following transformations. (4 points each)

Br

CH3
OH
OH
OH
H

12. Provide the product for the following reaction. Be sure to show the stereochemistry of the
product. (3 points)
Br Me
NaOH
OMe
Ph
H Me

5
13. Draw the mechanism for the following reaction, and write "slow" next to the rate
determining step. Be sure to draw all intermediates, and to correctly draw "electron-movement"
arrows or half-arrows. (4 points)

OH H2SO4, !
H

14. Draw the mechanism for the following reaction. Be sure to draw all intermediates, and to
correctly draw "electron-movement" arrows or half-arrows. (4 points)
Br
Br2 Br

15. Formula: C4H8

Reactivity: reacts with H2/Pt to give C4H10
DRAW ALL POSSIBLE ISOMERS, INCLUDING STEREOISOMERS. (4 isomers are
possible!) (5 points)

6
 73
1

JASPERSE CHEM 350 TEST 4 VERSION 1

Conjugation, Diels-Alder, Aromaticity, Aromatic Reactions

1. Provide the Name or Structure for the Following (7 points)

m-nitroaniline

CH3

Br

2. Circle the aromatic molecules (6 points)

O +

3. Outline the energies of the π-molecular orbitals for benzene, and draw electrons into the
orbitals that are occupied. (5 points)

Not Test Responsible this Semester

Nonbonding line ----------------------------------------

4. Bromide B has normal reactivity (for a 2º bromide) toward SN1 substitution, but A has much
higher reactivity and C has much lower reactivity. a) Why is A more reactive toward SN1? b)
Why is C much less reactive toward SN1? (4 points)
Br >> Br >> Br Kinetic reactivity toward
A B SN1 reactivity (H 2 O, H +)
C
 74
2

5. Synthesis Reactions. Draw the feature product of the following reactions (need not show any
byproducts). (21 points, 3 points each)

HNO3 , H 2 SO4
HO SO3H

Answer key shows

only one, but either
+ of two structural
O
isomers will be
accepted. (Carbonyl
on either spot 5 or 6)

1. HNO3 , H 2 SO4

2. Cl 2 , AlCl 3
3. Fe, HCl

1. Br 2 , hv

2. NEt 3 , heat

+ CN
NC

1. SO3 , H 2 SO4
CH3O
2. Br 2 , FeBr 3
3. H 2 O, H 2 SO4

1. Cl AlCl3

2. Zn(Hg), HCl
3.
Cl, AlCl3
(1 equivalent)
 75
3

6. Design sequences for the designated conversions. (5 points each)

CH3 CH3

NH2

Br

7. Design a synthesis for the following molecule beginning with toluene. (6 points)
Br

O 2N

CO 2H

8. Draw the Reactants for the Following (6 points)

Via Substitution
Not Test Responsible this Semester
for this Top problem. Problem below, on a Bromide
you are responsible. O

Via Diels-Alder
O
CH3O
O
 76
4

9. a) Draw the major product for the following reaction, and b) draw the mechanism for its
formation. c) Identify the slow step. d) Draw all the resonance structures for the cation
intermediate and e) circle the most important contributor. (7 points)

Cl2 , AlCl 3
H2N Cl

10. (9 points total) a) Draw the mechanism for the following reaction, in which a common
intermediate gives rise to both products.
OH Br Br
HBr
+
Ph Ph Ph
A B
optically active

b) In the above reaction, is product A chiral or achiral?

c) Product A is formed preferentially at low temperature, but B is major when the reaction is
conducted at high temperature such that product equilibration occurs. Which is the
“thermodynamic” product (more stable, so it builds up under equilibrating conditions) and which
is the “kinetic” product (less stable but forms preferentially under non-equilibrating conditions.)

Thermodynamic Control Product: Kinetic Product:

d) Draw the 2 relavant resonance structures for the key intermediate (or mark them if you
already drew both in your mechanism). Circle the one that would make the greater contribution
to the resonance hybrid. Why is the “kinetic” product formed preferentially under irreversible
conditions?
 77
5

11. Rank the following, with 1 being highest/most. (2 points each)

Heat of Hydrogenation

Reactivity Towards O

Reactivity toward
Br Br Br SN2 Substitution

Stability

O O
HN
Stability
NH

Reactivity toward
Br OCH3 HNO3 /H2 SO4

Reactivity toward
HBr addition

12. For each nitrogen in the molecule, classify the hybridization of the nitrogen atom, the
hybridization of the nitrogen lone pair, and classify whether the basicity of the nitrogen is
“normal” or “low”. (5 points)

Nitrogen Lone-Pair Nitrogen

Hybridization Hybridization Basicity
Na

Nb
H
a N N
Nc c NH2
N d
O
Nd b
H
78
 1 79

JASPERSE CHEM 350 TEST 4 VERSION 2

Conjugation, Aromatic Compounds, Reactions of Aromatic Compounds

1. Provide the Name of Structure for the following. (7 points)

a. 3-nitroaniline

b. o-isopropyltoluene

c. NH

2. Circle the aromatic molecules. (7 points)

NH •

3. The molecule has 3 different nitrogens. For each of them, classify the hybridization of the
nitrogen atom, the hybridization of the nitrogen lone pair, and whether the basicity of the
nitrogen is "normal" or "low". (6 points)

O
a Nc
N
H NH2
b
Nitrogen Lone-Pair Nitrogen
Hybridization Hybridization Basicity

Na

Nb

Nc
 2 80

4. Draw the major products of the following reaction (4 points).

H-Br

(no peroxides)

5. Draw the Major Product of the Following Reactions. Note: I want one major product in each
case. (3 points each)
CH3

Br2 , FeBr 3

1. HNO3 , H 2 SO4

2. Cl 2 , AlCl 3
3. Fe, HCl

1. Br 2 , hv

2. NaOH

O
OMe

1. Cl , AlCl3

2. Zn(Hg), HCl

Br

Answer key shows only

OMe heat one, but either of two
+ structural isomers will be
O
accepted. (Carbonyl on
either spot 5 or 6)

CH3 1. SO3 , H 2 SO4

2. HNO3 , H 2 SO4

3. KMnO4
4. H 2 O, H 2 SO4
 3 81

6. Rank the following, with 1 being highest/most. (2 points each)

Reactivity toward
OCH3 SO3H CH3
Br2 , FeBr 3

Heat of
hydrogenation

O O O

Stability
O O
O

OMe OMe

Combined
Diels-Alder
+ + + Reactivity
O

H H H Cation
Stability
+ Br + Br + Br
NH2 NO 2
NO 2

Reactivity
Br Br Br toward NaOMe

7. Outline the π-molecular orbitals of cyclopentadiene cation (use a Frost diagram), indicate
which are occupied by electrons, and indicate whether the species is unusually stable or not. (6
points)

Not Test Responsible this Semester

for this problem.

Nonbonding line ---------------------------------------------------------------------------------

 4 82

8. Treatment of an alkyl halide with methanolic AgNO3 often promotes ionization, via the
following:

R X Ag+ R+ + AgX

When 3-bromo-1-butene undergoes this reaction, two isomeric products A and B are formed.
Draw the structure for product B and the detailed mechanism for formation of product B. (7 pts)
Br OMe
AgNO3
+
MeOH
A
B

9. Draw the product for the following reaction and draw the mechanism for its formation.
Identify the slow step. Draw all the resonance structures for the cation intermediate and circle
the most important contributor. (7 points)
NO 2

Br2 , FeBr 3

Me
 5 83

10. (6 pt) When comparing cyclopentadiene (A) versus 1,3-pentadiene (CH2=CH-CH=CH-

CH3, B),

a. One is much more acidic. Which is it, and why?

b. One is a much more reactive diene. Which is it, and why?

11. Draw the Reactants for the Following Reactions (7 points)

Not Test Responsible for this
Via Substitution
top problem. (Problem
below you are) on a Bromide

Via
O
Diels-Alder
CN

12. Provide reagents for the following transformations. (5 points each)

Cl

NO 2

Br
84
 85
1

JASPERSE CHEM 350 TEST 4 VERSION 3

Conjugation, Aromaticity, Electrophilic Aromatic Substitution

1. Provide Either the Name or the Structure for the Following Chemicals. (6 points) (3
minutes)

a. Furan

b. p-nitrobenzoic acid

NH2

c.

2. For the following substituents, classify each as 1) electron-donating or electron-withdrawing

["D" or "W"], 2) as activating or deactivating ["Act" or "Deact"], and as 3) ortho-para directing
or meta directing ["o/p" or "m"]. (6 points) (2 minutes)

-OCH3 - CCH2CH 3 -CH3 -Cl

 86
2

3. Rank the reactivity (rates!) of the following sets of molecules toward the reagents shown, 1
being most reactive, 2 being middle, and 3 being least reactive. (10 points) (6 minutes)

Reagent Molecules Being Compared

a. H2 , Pt

Br

Br
b. H+, H 2 O (SN1/E1)

Br

c.

NO2 Cl CH3

d. HNO3 , H 2 SO4

Br

f. NaOMe
(SN2 reactivity) Br Br
 87
3

4. Draw the major product for each of the following reactions. (3 points each, 21 total, 7
minutes)

NO2

Cl2 , AlCl 3
a.

Br

1. SO3 , H 2 SO4
b.
2. HNO3 , H 2 SO4
3. H 2 O, H 2 SO4

OCH2 CH3

1, HNO 3 , H 2 SO4
c.
2. Fe, HCl

Br

1. Br 2 , hv
d.
2. NaOMe

O
Cl2 , FeCl 3
e. O2N C CH3

Br
1. Mg, ether Not Test Responsible for this problem.
f.
2.
Br

CO2Me
heat
g. +
MeO 2C
 88
4

5. Provide reagents for the following transformations. (5 points each, 10 total, 6 minutes)

CH3 CO2H
a.

Cl

b.

NH2

6. Daw the diene and dienophile from which the following Diels-Alder products would have
come. (3 points each, 6 total, 2 minutes)

CN
heat
a.
Me2N CH3

MeO O
H
heat
b. O

H O
 89
5

7. a. Draw the mechanism for the formation of the major product shown, and identify the
"slow" step in the reaction. (6 points, 5 minutes)
O
O
AlCl3
+
Cl
MeO MeO

b. Draw all 4 resonance structures for the cation intermediate in the above reaction, and circle
the most important contributor. (4 points)
 90
6

8. Draw the major product or products that would result from the following reaction, and write
either "chiral" or "achiral" and "optically active" or "racemic" by each product. Draw a
mechanism for the reaction, and identify the "slow" step in the reaction. (8 points, 5 min)

+ 1.0 HBr

9. Provide a synthesis for the following molecule, using benzene and anything else you like.
"Backwards syntheses" are fine, so long as you draw the reagents! (7 points, 5 min)

Br

NO2
 91
7

10. Circle the aromatic molecules: (6 points) (3 minutes)

+ N:

OH

HN

11. The molecule below has 3 different nitrogens. For each of the nitrogens, classify the
hybridization of the nitrogen atom, the hybridization of the nitrogen's lone pair, and whether the
basicity of the nitrogen is "normal" or "low". (6 points, 2 min)

NH2
a N N c
b
.
Nitrogen Lone-Pair Nitrogen
Hybridization Hybridization Basicity

Na

Nb

Nc

12. Outline the energies of the π molecular orbitals of cyclobutadiene (use a Frost diagram),
indicate which are occupied by electrons, and indicate whether the molecule is "unusually stable"
or not. (4 points, 1 min)

Not Test Responsible for this problem.

Nonbonding Line
92
 93

JASPERSE CHEM 350 FINAL EXAM VERSION 1

150 points total

1. Provide names or structures for the following. 2 points each. Specify stereochemistry when
appropriate!

Cl CH3

Br

m-isopropylphenol

Cl

HO

2. Identify the functional groups in the following molecule. (4 points)

O

OCH3

1
 94

3. Predict the major products for the following reactions. Pay careful attention when orientation
is a factor. Draw just one major product in each case. (3 points each)

CN
+
CN
OCH3

Br2 , hv

NaOCH3
Br

1. O3

2. Me2S

HBr

OsO4, H2O2

O 1. Br2, FeBr3
2. Zn(Hg), HCl

3. Br2, hv

1. H2O, Hg(OAc)2

2. NaBH4

2
 95
3

4. Classify the pairs of molecules as totally different, identical, structural isomers,

diastereomers, or enantiomers. (2 points each)

Br

Br Br Br

Br

Br Br Br

Cl CH3 Cl H

Br H Br CH3

5. Classify each chiral carbon as R or S. (2 points each)

HO H

H
CH3

6. Classify the hybridization and bond angles (109, 120, or 180) at the labelled atoms. (5 points)
O
4
2 OH
1 3

C-1 C-2 C-3 O-4

3
 96
4

7. Draw the mechanisms for the following reactions. For any radical reactions, draw
propagation steps only. 5 points each.

OCH3 OCH3
Cl2

AlCl3
Cl Draw the resonance structures for the cation intermediate.

H H H Br
Br2 , hv
Ph Ph

Br2 , H 2 O Br

OH

4
 97
5

8. Draw the products of the following multi-step sequences. (4 points each)

Me Br 1. NaOH

2. HBr, peroxides
Ph 3. NaOMe

CH3 1. SO3, H2SO4

2. 2-bromopropane, AlCl3

3. H2O, H+

OH 1. H2SO4
2. HBr, Peroxides

3. NEt3

9. Draw as many structural isomers as you can for C6H14. Circle any that are chiral. (Note: be
careful! You will lose points for any repeats!) (6 points)

5
 98
6

10. Rank the Following, from most to least. 2 points each.

Cl
a. Reactivity toward S N2 Br

I Cl

•
b. Stability •
• •

CH3 H
c. Stability H CH3
H
Me2CH H
CH3
H Me2CH Me2CH

d. Acidity PhCO2 H (CH3 )2 NH HCl CH3 CH2 OH

Me HMe Me Me
H H Me H Me
e. Stability
H H H H
H H H
Me H H
H HH
Me

OH OH OH
f. Reactivity toward
H2 SO4 /Î catalyzed
dehydration

OH
g. Boiling Point
OH

6
 99
7

11. Provide reagents for the following transformations. You may use anything you like. Each
can be done within ≤3 steps. (4 points each)

Br
OH

Br

H2N Br

12. Provide the appropriate reactant for the following transformation. (3 points)

H OH
CH3 CO3 H, H 2 O

HO H

7
 100
8

13. Suggest a structure for X, given the following info: (5 points)

• Formula: C8H12O
• It Reacts With excess H2/Pt to produce C8H16O
• When it reacts with O3/Me2S, one of the products is CH2=O.

14. Which of the following are aromatic

H
N

15. Draw the products and mechanism for the following reaction:

1 H-Br

16. Rank the following:

O Combined
O O
Diels-Alder
+ O Reactivity
+ + O
O
O

Br Cl Br Combined
+ + O + O SN2
Reactivity
ONa ONa ONa

8
 1 101

JASPERSE CHEM 350 FINAL EXAM VERSION 2

Note: Good for practice, but significantly longer than the real one will be.

1. Rank the Following, from most to least. 2 points each.

a. Stability

•
b. Stability
• • •

c. Stability CH3 H H CH3

H H H CH3 H

d. Acidity CH3OH PhCO2H NH3 CH3CH3

Me HMe Me MeMe
H H Me H
e. Stability
H H H H
H H H
Me H
H HH
Me H
 2 102

f. Reactivity toward HBr

g. Reactivity toward Br 2 /hv

Cl
h. Reactivity toward SN2 Ph I Ph Br Ph Cl
Ph

OH
i. Boiling Point OH

j. Stability

2. Provide names or structures for the following. 3 points each. Note: don't forget to specify
stereochemistry!

a. CH3

H3 C

b.
 3 103

c. optically actve
OH

d.
Br

OH
e.

f. trans-1-bromo-3-isopropylcyclopentane

3. Classify the pairs of molecules as totally different, identical, structural isomers,

diastereomers, or enantiomers. (2 points each)

a.

Br Br Br Br

Br Br Br
b.

Br

Br Br
c.

Br Br
 4 104

3. (continued) Classify the pairs of molecules as totally different, identical, structural isomers,
diastereomers, or enantiomers. (2 points each)

d.

e.

f.

Br Br Br Br

OH OH
f.

4. Draw at least four different isomers for C5H10. (There are lots more than four…) (6 points)

5. (a) Draw the appropriate number of lone pairs on the oxygen atom,
(b) Assign a formal charge on oxygen if appropriate,
(c) Draw an additional resonance structure for the following, and
(d) Identify which of the two structures would make the greater contribution to the hybrid. (4
points)

O
 5 105

6. Draw resonance structures for each of the following:.

7. Identify the functional groups in the following molecule. (4 points)

HO OH
N
O H

8. Classify the hybridization and bond angles (109, 120, or 180) at the labelled atoms. (4 points)

2
O
1 3

C-1 O-2 C-3

9. Draw both chair conformations of trans-1-methyl-3-isopropylcyclohexane, and circle the

more stable one. (5 points.)
Note 1: It will simplify things if you abbreviate the isopropyl group as "R".
Note 2: Make sure that your second chair has the same "configuration" as the first, and is not an
enantiomer.
 6 106

10. Classify each chiral carbon as R or S. (Some structures may have more than one chiral
carbon!) (2 points each)

a.
H OH

O
b
H
CH3

11. Mechanisms Problem. Draw the mechanism for the following reactions, and write "slow"
next to the rate-determining step. Be sure to draw all intermediates, and to correctly draw
"electron-movement" arrows or half-arrows. For radical reactions, draw propagation steps only.
4 points each.

OH
a. H2O, H+

Br2 Br
b.
Br
 7 107

Mechs, continued

Br
Br2, hv
c.

H Br H+ (catalyst) H OH
d.
Ph Ph
H2O
 8 108

12. Predict the major products for the following reactions. In each case, pay careful attention to
orientation and stereochemistry. Draw just one product in each case. (3 points each)

HBr
a.

H2 O, H +
b.

H ONa CH3 CH2 I

c.

a. O3
d.
b. Me2S

e. Br2, hv

NaOCH3
f. Br

1. BH3-THF
g.
2. NaOH, H2O2

1. NEt 3
h.
Br 2. Cl2
 9 109

13. Draw the substitution products for the following reactions. (Do not draw any accompanying
elimination products.) Include stereochemistry in your answer, and if two substitution products
are formed, draw them both. Assume the starting material is optically active as drawn. (3 points
each)

H Br
NaOMe
a.
Ph

Me Br
H2 O,
b.
Ph cat. HBr

14. Draw the products of the following multi-step sequences. (4 points each)

1. H2SO 4
a.
OH 2. CH3 CO3H, H2O

1. Br2, hv
Me H 2. NEt3
b.
Ph 3. CH3CO 3H, H2 O
 10 110

15. Provide reagents for the following transformations. More than one step is needed in each
case. (4 points each)

Br Br

a. Br

H
OH
b. O

16. Provide the appropriate reactant for the following transformation. (3 points)

Br H
Br2, H 2O

HO H

17. Suggest a structure for A that is consistent with the following information. (There is more
than one possible solution, but you only need to provide one.) (5 points)
1. O3
A C + C2 H4 O
C7 H1 2 2. Me2 S C5 H8 O
achiral
achiral
H2 , Pt

B
C7 H1 4
achiral
 11 111

18. Draw the products for the following reactions:

1 H-Br

a.

NBS,

b. peroxides

O heat
+ O

c. O

H2O

Br Draw substitution
d. product(s) only

1. Br2, FeBr3

2. HNO3, H2SO4
e.

1. + AlCl3
Br

2. KMnO4
f.

1. SO3, H2SO4
O

Br 2. Cl + AlCl3

3. H2O, H+
g. 4. Zn(Hg), HCl

1. Br2, hv

2. NaOCH3
h.
 12 112

19. Which of the following are aromatic

20. Classify the lone pair hybridization on the three nitrogen atoms in the following molecule:

b Na
N
NCH3 Nb
H2N c
a Nc

21. Draw the major products and mechanism for the following reaction:

1 H-Br

Ph

22. Draw the major product and mechanism for the following reaction. Draw all of the
resonance structures for the key carbocationic intermediate

HNO3,

O2N H2SO4
 13 113

23. Design a synthesis for the following:

O2N

24. Explain why A is more acidic than B, but C is less reactive than D towards SN1 reactivity
Br
Br
> Acidity SN1 Reactivity
<
A B
C D

25. Rank the following

O
CH3 OCH3 Reactivity
toward
Cl2, AlCl3

O O
O Combined
Diels-Alder
+ + + Reactivity

Stability
114