Organic Chemistry ACS Sample Questions

ACS Examination guide (Selected Questions)
Organic Chemistry
Nomenclature
1. What is the IUPAC names for this compound?
a) 1-tert-butyl-2-butanol
b) 5,5-dimethyl-3-hexanol
c) 2,2-dimethyl-4-hexanol
d) 1,1,1-trimethy-3-pentanol
4.What is the IUPAC name for this structure?
a) 3-bromo-4-methylheptanone
b) 5-bromo-4-methylheptanone
c) 5-bromo-4-methyl-3-heptanone
d) 3-bromo-4-methyl-5-heptanone
9. What is the IUPAC name of this compound?
a) m-hydroxy-m-xylene
b) 3,5-dimethylphenol
c) 2,4-dimethyl-6-hydroxybenzene
d) 3-hydroxy-5-methyltoluene
Answer: 1, b; 4, c; 9, b.
Structure, Hybridization, Resonance, Aromaticity Chapter Book p 17,18,19
1) identify the lowest-energy Lewis structure for nitrogen oxide. (Formal charges not
shown.)
8) The heat of combustion (per CH2) of several cycloalkanes is listed below. Based on
the data given, which of these cycloalkanes would be considered most stable.
a) cyclobutane b) cyclopentane c) cyclooctane d) cyclopentadecane
11) Which pair consists of the resonance structure?
Answer: 1, c; 8, d;11, a
Organic Chemistry (/organic-chemistry/practice-problems) / Factors Affecting Acidity Overview (/organic-
chemistry/factors-affecting-acidity)
Acid and Videos

Concept Bases(/organic-chemistry/factors-affecting-acidity)
Book P 30, 31 Solutions 28
1. Which structure corresponds to the predominant form of this molecule near pH 7?
1x 1.25x 1.5x 1.75x 2x
Solution: Which is the order from the strongest acid to the weakest ac...
Question
Which
4. is the
Which order
is the fromfrom
order the strongest acid toacid
the strongest the weakest acid for these
to the weakest species?
acid for these species?
A) II > IV > I > III
B) III > I > IV > II
C) III > IV > I > II
D) II > I > IV > III

8) Which of the indicated protons in this compound would have the smallest pKa
values?
Answer: 1, c;4, a;8, d.

Stereoisomerism Book P38, 39,
1) Which molecule has the R configuration?
6) Which Newman projection represents the most stable configuration of

(CH3)2CHCH(CH3)2
10) Which diastereoisomer is most stable?
Answer: 1, c; 6, c, 10, b.
Nucleophilic Substitution and Elimination
2) When 2-bromo -2-methybutane is treated with a base, a mixture of 2-methyl-2-butene
and 2-methyl-1-butene is produced
When potassium hydroxide is the base, 2 methyl-1-butene accounts for 45% of the
mixture, but when potassium tert-butoxide is the base, 2 methyl-1-butene accounts for
70% of the mixture. What would you predict for the percent of 2 methyl-1-butene in the
mixture if the potassium prop-oxide were the base?
(a) Less than 45%
(b) 45%
(c) between 45% and 70%
(d) more than 70%

11) Why would the concentrated hydrobromic acid be an inappropriate catalyst for the
dehydration of alcohols?
a) HBr is too weakly acidic to protonate the alcohol.
b) The conjugate base, Br - , is a good nucleophile and it would attack the carbocation
to form an alkyl bromide.
c) HBr is strongly acidic, so the water molecule would not be a good leaving group after
protonation of the alcohol.
d) HBr would be more likely to promote rearrangement of the carbocation intermediate.
17) What would be the first step in the dehydration of cyclohexanol in sulfuric acid?
a) loss of OH -
b) loss of H+ by the alcohol
c) formation of a sulfite ester
d) protonation of the alcohol
Answer: 2, c, 11, b, 17, d.

Electrophilic Additions
7) which set of the reagents will carry out the conversion shown?
Answer: 7, c
Nucleophilic Addition at Carbonyl Groups
8) which compound would be most rapidly hydrolyzed by aqueous HC to give methanol
as one of the products?

12) which is the best reagent for this conversion?
17) which reagent will accomplish the conversion shown?
Answer: 8, d, 12, b, 17, d.

Nucleophilic Substitution at Carbonyl Groups
1) This reaction that is typical of carboxylic acids, ester, acid halides, anhydrides, and
amides is called.
(a) nucleophilic non-acyl substitution
(b) nucleophilic addition
(c) nucleophilic acyl substitution
(d) electrophilic substitution
3) Which would be hydrolyzed most slowly with aqueous NaOH?

13) Which reaction sequence is preferred for this conversation?
Answer: 1, c, 3, a, 13, b.
Enols and Enolate Ion Reactions pg. 97
16) The first two steps in the base-catalyzed condensation of acetaldehyde would be
described as:
–
D) OH abstracts the hydrogen atom from the carbonyl carbon, the then resultant anion attacks
the carbonyl carbon atom on a second molecule of acetaldehyde.
20) Which represents a keto-enol tautomerization?
24) What is the product formed from this reaction?
Answer: 16, c; 20, d; 24, d.

Electrophilic and Nucleophilic Aromatic Substitutions pg.114
1. Which substituents would deactivate benzene toward electrophilic aromatic

substitution reaction?
4. Which set of reagents would most likely bring about this transformation?
Answer: 1, b; 4, a.
Free-Radicals Substitution and Additions
1. Which radical is the least stable?
5. What is the expected product of this reaction?
Answer: 1, b; 5, c.
Oxydation and Reduction pg. 138
1. which reagents are best for carrying out this reaction?
3. Which reagents would best accomplish this transformation?

6. reduction of a triple bond to a E (trans) double bond can be accomplished with wich
set of reagents?
Answer: 1, a; 3, c; 6, a.
Spectroscopy
1. Which ketone will show a carbonyl absorption at the lower frequency (cm-1) in the
infrared?
3. Which is the reasonable structure for a compared with this IR spectrum?
5. Which structure is most consistent with this IR spectrum?
Answer: 1, b; 3, a; 5, d.
Synthesis and Qualitative Analysis
12. Which would be a suitable solvent for the preparation of ethyl-magnesium

bromide from ethyl bromide and magnesium?
14. Which reaction sequence might be used to synthesize this compound?
Answer: 12, c; 14, a.

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ACS Examination guide (Selected Questions)

1. What is the IUPAC names for this compound?

4.What is the IUPAC name for this structure?

9. What is the IUPAC name of this compound?

a) cyclobutane b) cyclopentane c) cyclooctane d) cyclopentadecane

11) Which pair consists of the resonance structure?

Acid and Videos

1. Which structure corresponds to the predominant form of this molecule near pH 7?

1x 1.25x 1.5x 1.75x 2x

A) II > IV > I > III

B) III > I > IV > II

C) III > IV > I > II

D) II > I > IV > III

Answer: 1, c;4, a;8, d.

1) Which molecule has the R configuration?

6) Which Newman projection represents the most stable configuration of

2) When 2-bromo -2-methybutane is treated with a base, a mixture of 2-methyl-2-butene

and 2-methyl-1-butene is produced

mixture if the potassium prop-oxide were the base?

(a) Less than 45%

(c) between 45% and 70%

(d) more than 70%

a) HBr is too weakly acidic to protonate the alcohol.

to form an alkyl bromide.

protonation of the alcohol.

d) HBr would be more likely to promote rearrangement of the carbocation intermediate.

b) loss of H+ by the alcohol

c) formation of a sulfite ester

d) protonation of the alcohol

Answer: 2, c, 11, b, 17, d.

Nucleophilic Addition at Carbonyl Groups

8) which compound would be most rapidly hydrolyzed by aqueous HC to give methanol

as one of the products?

17) which reagent will accomplish the conversion shown?

Answer: 8, d, 12, b, 17, d.

(a) nucleophilic non-acyl substitution

(b) nucleophilic addition

(c) nucleophilic acyl substitution

(d) electrophilic substitution

3) Which would be hydrolyzed most slowly with aqueous NaOH?

Enols and Enolate Ion Reactions pg. 97

24) What is the product formed from this reaction?

Answer: 16, c; 20, d; 24, d.

1. Which substituents would deactivate benzene toward electrophilic aromatic

1. Which radical is the least stable?

5. What is the expected product of this reaction?

1. which reagents are best for carrying out this reaction?

3. Which reagents would best accomplish this transformation?

12. Which would be a suitable solvent for the preparation of ethyl-magnesium

14. Which reaction sequence might be used to synthesize this compound?

Answer: 12, c; 14, a.

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