FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry & Biochemistry CHM 2210-U02 ORGANIC CHEMISTRY I Fall 2012

PRACTICE EXAM I

CHM 2210-U02, Fall 2012 Practice Exam I, Page 2 FLORIDA INTERNATIONAL UNIVERSITY Department of Chemistry Dr. Keller PRACTICE EXAM I CHM 2210-U02 Fall 2012

MULTIPLE CHOICE QUESTIONS: Answer each of the following questions by bubbling in the correct response on the Scantron answer sheet. 1. Which of the following is the Lewis structure for CH3CH2O2H?
H H H C C O O H a. H H
: : : :

3.

Which one of the following structures is not identical to the others?

H H c. H C O C O H

a.

c.

CH3 C

CH2

:
H
H
: :

H
CH3CH2

H
:

H
: :

H H O

b. H C O C O H H

d. H C C C O H H H

b.

CH2

d.

CH3CH2 CH3

CH3 C

CH CH3

CH3CH2CHCH3

H O H
e. H C C O H H H

:
:
CH2CH3

:
e.

CH CH3

CH3CH2CH2

2.

How many ester functional groups are in the potent anticancer compound Taxol?

O
O
O
N H

4.

O
O

Which of the following cannot be a correct Lewis structure?

OH
a.

:O :: N:: O:

:
H :F :

OH

O
O

Taxol

b. : F : C : F :

: :

:F:

: : :

:
d.

H:C::C:H

a. 0

b. 2

c. 3

d. 4

e. 5

e. All are correct

CHM 2210-U02, Fall 2012 Practice Exam I, Page 3 5. Which of the following represent proper resonance structures for CH2N2?
H

8.

Guanacastepene is a natural product that was recently isolated and shown to be a potent antibiotic. How many different functional groups does this structure possess?

:
a.
H:C:N:::N:

c.

H:C::N:N:

CH3
CH3

b.

H:C::N::N:

:
H

d.

H H:C::N::N:H

HO

O
O
O

: :

e. both a and b are correct.

Guanacastepene
a. 1 b. 2 c. 3 d. 4 e. 5

6.

Which of the following structures must be incorrect?

OH

9.

a.
Cl

c.

Which compound is not a constitutional isomer of the others?

CH3 O

a.
d.

c.

H N

b.

b.
e.
C C

N O

d.
N

7.

Which of the following molecules contain both an alcohol and an aldehyde functional group?
O

e. All of the above are constitutional isomers of each other.

a.

O
O
OH
c. HO

NH2

10. The formal charge on sulfur in sulfuric acid is:

O
O

b.

OH

HO S OH

CO2H
e.
O

H N

a. 0

b. -1

c. +1

: :

: :

: :

d. -2

e. +2

CHM 2210-U02, Fall 2012 Practice Exam I, Page 4 11. What is the molecular formula of limonene, the major volatile compound in orange peel oil? 15. What would be the bond-line form of the following condensed structure?

CH3CH2CH(CN)CH=CH2
Limonene

a. b. c. d. e.

C10H18 C10H20 C10H16 C11H14 C11H18

a.
N

c.

b.

HN

d.
N

12. Expansion of the valence shell to accommodate more than 8 electrons is possible with: a. Fluorine c. Carbon b. Nitrogen d. Sulfur e. Beryllium
e.
N

d. Two of these e. All of these

14. Which of the following structures is not a resonance form of the following species?
:O

:O

a.

c.

:O

b.

:O

d.

:O

e. They are all resonance structures.

:
: :

13. Which of the following is an ion with a net -1 charge? O a. O CH3 c. O N b. O N O O

: :

16. Which of the following is not a resonance structure of the others?

: :

OCH3
H

OCH3

a.

c.

H
:

H
OCH3

OCH3
H

b.
:

d.

H
:

OCH3

e.
:

CHM 2210-U02, Fall 2012 Practice Exam I, Page 5 17. In which structure(s) below does the oxygen have a formal charge of +1?
H O H H I H H C O H III H O II CH3 O CH3 CH3 IV

19. Which is an acceptable Lewis structure for methyl azide?

H
:

a. H

C N H H

N N:

c. H

C N H

N N:

H
:

b. H

C N H

N N:

d. H

C N H

N N:

a. I only b. II only c. I and III

d. I and IV e. I, III, and IV

18. What is the correct line-bond representation for the following condensed structural formula?
CH3CH2CH(CH3)CH2C(CH3)2CH(CH2CH3)CH(CH3)2

a.

b.

c.

d.

e. None of these is correct.

20.

22.

1.

The following electron configuration represents _______

3.

The process of adding electrons one by one to atomic orbitals beginning with the lowest energy is described by: a. the Aufbau Principle

sp3 1s

sp3

sp3

sp3

b. Hunds Rule c. the de Broglie Relation d. the Pauli Exclusion Principle

a. b. c. d. e.
21.

the ground state of boron. the sp3 hybridized state of carbon. the sp3 hybridized state of nitrogen. the bonding molecular orbital of carbon. the antibonding molecular orbital of carbon. Which is the strongest acid?
a.
23.

e. Coulombs Law

4.

In the following molecule, how many carbon atoms are in the sp3 hybridization state?
O

2.

CH2CH2CH2CH2CH2CO2H Cl

OCH3

a. 2
Br

b. 4

c. 5

d. 6

e. 11

b. CH3CHCH2CH2CH2CO2H

Br

24.

c.

CH3CH2CH2CCH2CO2H Br

5.

What would be the expected value of the indicated bond angle?

d. CH3CH2CH2CHCH2CO2H

F
F
e.

CH3CH2CH2CCH2CO2H F

Br

a. 120

b. 90

c. 104

d. 180

e. 109.5

25.

6.

Which of the following statements is(are) true of sp orbitals? a. Orbitals of the sp type have 50% s-character and 50% p-character. b. They are hybrid orbitals. c. They are linear with respect to each other. d. They result when one s-orbital and one p-orbital are mixed. e. All are correct.

26.

7.

What is the hybridization of the each of the labeled atoms for the potent neurotoxin Gephyrotoxin?
A

D
H

B
H

H
N

E
OH

Gephyrotoxin

28.

11. Arrange these acids in the order of increasing acidity a. b. c. d. e.

A = sp2, B = sp, C = sp2, D = sp3, E = sp3 A = sp , B = sp, C = sp , D = sp , E = sp

SiH4

H2S

HCl

PH3

A = sp2, B = sp, C = sp2, D = sp3, E = sp2 A = sp2, B = sp, C = sp3, D = sp3, E = sp3 A = sp, B = sp, C = sp3, D = sp3, E = sp3 Which of the following is not considered a Lewis acid?
a. H b. CH3OH2 e. BF3 c. AlCl3
CH3 C
29.

a. SiH4, H2S, HCl, PH3 b. HCl, H2S, SiH4, PH3 c. HCl, H2S, PH3, SiH4 d. SiH4, PH3, H2S, HCl e. PH3, SiH4, H2S, HCl 12. Expansion of the valence shell to accommodate more than 8 electrons is possible with: a. Fluorine c. Carbon b. Nitrogen d. Sulfur e. Beryllium

8.

d.

CH3

CH3

30.

33.

13. Does the equilibrium of this reaction lie to the right or to the left?
ClCH2CH2OH + CH3CHO :

16. Consider the following 4 alkenes:

a. To the right b. To the left c. It cannot be determined without pKa data.

14. Which molecular shape is not represented in the following group of molecules?
:

:O:

CH3 S

a. linear b. bent c. pyramidal d. trigonal planar e. tetrahedral

15. Identify the atomic orbitals which are overlapping to form the C-2---C-3 sigma bond (indicated by the arrow) in the following molecule:
4 5 3 1 2

a. sp2,sp2 b. sp2,sp

: :
Cl

CH3 : O
: :

ClCH2CH2O : + CH3CHOH

Cl

CH3CH2CH=C(Cl)CH2CH2CH3
III

CH3C=CHCH2CH2CH2CH2CH3 CH3
IV

:O:
: :

Which structures can exist as cis/trans isomers?

: Cl :
: :

O:
:

: Cl
:

P
:

a. I and II b. I and III

c. I and IV d. II and III

O
:

O
:
6

S
:

S
:

e. I, III, and IV 17. The conjugate base of sulfuric acid is: a. H3SO4 b. SO4 2
+

c. HSO4

d. H2SO3 e. HSO3 -

35.

18. What is the spatial arrangement of the methyl anion ( :CH3 )? a. Octahedral b. Tetrahedral e. Pyramidal
36.

c. Trigonal planar d. Linear

19. Which of the following is not a BronstedLowry acid? a. H2O b. (CH3)3N e. HC CH c. NH4 d. CH3CO2H
+

c. sp2,sp3 d. sp3,sp2 e. sp,sp2

37.

20. Which pair of species are both bases in the following reaction:

HCN + H2O

CN + H3O

a. H2O and CN b. H3O and H2O c. HCN and H3O d. HCN and CN e. H3O and CN
38.

21. Which of these is not a Lewis acid? a. AlBr3 b. BCl3 c. Ph3P + d. H

e. All are Lewis acids

22

Which of these is not a true statement? a. All Lewis bases are also Bronsted-Lowry bases. b. All Lewis acids contain hydrogen. c. All Bronsted-Lowry acids contain hydrogen. d. All Lewis acids are electron-deficient. e. According to Bronsted-Lowry theory, ammonia is both an acid and a base.

41.

25. Which base would completely remove a proton from phenol (C6H5OH)? a. NaCl
42.

b. H2O - + d. CH3CH2O K

- + c. CH3CO2 Na
e. All of the above.

26. Which one of the following is a true statement? a. The stronger the acid, the larger is its pKa. b. The conjugate base of a strong acid is a strong base. c. Acid-base reactions always favor the formation of the stronger acid and the stronger base. d. Strong acids can have negative pKa values. e. Hydrogen need not be present in the molecular formula of a Bronsted-Lowry acid.

40.

23. Which acid/base reaction would not take place in the direction written?
a. CH3CH2Li + CH3CH2OH
b. HC
c. HC

CH3CH3 + CH3CH2OLi
HC
HC

CH + NaOH
CNa + H2O

CNa + H2O
CH + NaOH

d. CH3CH2OH + NaH

CH3CH2ONa + H2

e. CH3CO2H + CH3CH2ONa

CH3CO2Na + CH3CH2OH

43.

27. Which anion is the strongest base?

c. Cl d. CH3CH2O

28. When acid-base reactions reach equilibrium, there have been formed: a. b. c. d. the weaker acid and the weaker base. The weaker acid and the stronger base. The stronger acid and the weaker base. All acid-base reactions go to completion; they are not equilibrium processes.