Organic Chemistry

Carey/Giuliano

Chapter 8

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Question 1

Rank the following alkenes in order of

decreasing heat of hydrogenation.

A) 1>3>2
B) 3>2>1
C) 2>3>1
D) 1>2>3
Question 2
The heat of hydrogenation of cis-2-pentene is
117 kJ/mol. For which one of the following
alkenes has the heat of hydrogenation
126 kJ/mol?
A) 1-pentene
B) trans-2-pentene
C) 2-methyl-1-butene
D) 2,3-dimethyl-2-butene
Question 3

Which of the alkenes below will produce

2-methylbutane on catalytic hydrogenation?

A) 1 and 3
B) 1, 2 and 3
C) 2 and 4
D) 2, 3 and 4
Question 4

Which one of the following terms best applies

to the hydrogenation of an alkene in the
presence of finely divided platinum? (in
ethanol as solvent)
A) anti addition
B) Concerted reaction
C) heterogeneous catalysis
D) endothermic reaction
Question 5

Which alkene has the lowest heat of

hydrogenation?

A) B)

C) D)
Question 6

How many alkenes produce 3-ethylpentane on

catalytic hydrogenation?
A) 2
B) 3
C) 4
D) 5
Question 7

Which carbocation forms when

3-methyl-2-pentene is protonated?

A) B)
Question 8

The reaction of 3-methyl-1-butene with HBr

produces 2-bromo-3-methylbutane and
which other alkyl halide?

A) B)

C) D)
Question 9

What is the product of the reaction of

1-methylcyclohexene with HCl?

A) B)

C) D)
Question 10

What is the correct IUPAC name of the

compound isolated from the reaction of
2-methyl-2-pentene with HBr?
A) 3-bromo-4-methylpentane
B) 2-bromo-2-methylpentane
C) 3-bromo-2-methylpentane
D) 2,3-dibromo-2-methylpentane
Question 11

Which alkene reacts with HCl (electrophilic

addition) at the fastest rate?

A) B)

C) D)
Question 12

The product isolated from the acid-catalyzed

hydration of (Z)-3-methyl-2-pentene is:
A) 2-ethyl-2-butanol
B) 2-ethyl-1-butanol
C) 3-methyl-2-pentanol
D) 3-methyl-3-pentanol
Question 13

Which alkene will undergo acid-catalyzed

hydrolysis at the fastest rate?

A) B)

C) D)
 Question 14
Which combination of reagents is the best choice for carrying out
the conversion shown?
A) 50% water - 50% sulfuric acid
B) 1. H2SO4
2. H2O, heat
C) 1. O3
2. H2O, Zn
D) 1. BH3-THF
2. H2O2, NaOH
Question 15

Hydroboration-oxidation of which one of the

following yields a primary alcohol as the
major product?
A) B)

C) D)
Question 16

What is the product of the addition of Br 2 to

cyclopentene?

A) B)

C) D)
Question 17
Arrange the alkenes in order of decreasing rate
of reaction toward bromine addition:
2-methyl-1-butene, 2-methyl-2-butene, and 3-
methyl-1-butene
A) 2-methyl-1-butene > 3-methyl-1-butene
> 2-methyl-2-butene
B) 3-methyl-1-butene > 2-methyl-1-butene
> 2-methyl-2-butene
C) 2-methyl-2-butene > 2-methyl-1-butene
> 3-methyl-1-butene
D) 2-methyl-2-butene > 3-methyl-1-butene
> 2-methyl-1-butene
Question 18

Which reagent reacts with an alkene to

produce an epoxide?

A) B)

C) D)
Question 19

The ozonolysis of 2,4-dimethyl-2-pentene will

produce:

A) B)

C) D)
Question 20
Which one of the following is not
stereoselective?
A) reaction of cis-2-butene with
peroxyacetic acid
B) addition of Br2/H2O to
1,2-dimethylcyclopentene
C) addition of Br2 to trans-2-pentene
D) addition of HBr to cis-2-butene.
 Question 21
Which one of the following outlines the best synthesis of trans-2-
chlorocyclohexanol?
A) Heat a mixture of cyclohexanol and Cl 2 to 400oC.
B) 1. Treat cyclohexene with HCl;
2. Treat product of reaction 1 with peroxyacetic acid.
C) 1. Hydrogenation of cyclohexene in the presence
of Pt;
2. Treat product of reaction 1 with Cl 2 in H2O.
D) 1. Treat bromocyclohexane with KOC(CH 3)3 in
DMSO;
2. Treat product of reaction 1 with Cl 2 in water.
Answer Key – Chapter 8
1. A 11.C 21. D
2. A 12.D

3. A 13.D

4. C 14.D

5. C 15.A

6. A 16.A

7. B 17.C

8. B 18.C

9. A 19.B

10.B 20.D
 EXTRA 1: how many products can be
obtained from the following reaction.
Indicate the major product.

A) 3
B) 5
C) 6
D) 2
ANSWER 1: B 5 products
EXTRA 2: which of the following is the
best method for the following
retrosynthesis

A) CH3OH  Br2
B) CH3OH  Br2, H2O
C) CH3ONa  H2O
D) CH3ONa  Br2, H2O
ANSWER: D
EXTRA 3: what is the best method to
go from 3-methyl-2-butanol to 2-
methyl-2-butanol