Question 1

Which of the following best describes the mechanism for the reaction of cyclohexene with $$Br_2$$, $$H_2O$$ followed by $$NaOH$$, $$H_2O$$?

Accepted Answer

Anti addition of bromine followed by nucleophilic substitution with hydroxide, resulting in trans diol formation.

Question 2

What is the major product when cyclopentene is treated with $$m-$$CPBA in $$CH_2Cl_2$$?

Accepted Answer

An epoxide: cyclopentene oxide.

Question 3

When 1-methylcyclopentene is treated with $$HBr$$, what is the predominant product?

Accepted Answer

1-bromo-1-methylcyclopentane (Markovnikov addition).

Question 4

Which reagent would convert 1,2-dimethylcyclopentene to the corresponding trans-1,2-diol?

Accepted Answer

$$OsO_4$$, $$NMO$$, acetone, $$H_2O$$

Question 5

A student treats 1-phenyl-1-propene with $$NaOMe$$, $$EtOH$$ followed by $$H_2O. $$What is the major product?

Accepted Answer

Trans-stilbene alcohol ($$C_6H_5CH=CHCH_2OH)$$

Question 6

Which of the following best explains the stereochemistry of the product when cyclohexene is treated with $$OsO_4$$, $$NMO$$, acetone, $$H_2O$$?

Accepted Answer

Syn addition of two hydroxyl groups to the same face of the double bond.

Question 7

What is the expected product when 1,2-dimethylcyclohexene is treated with $$O_3$$ followed by $$Me_2S$$?

Accepted Answer

Two ketones formed by oxidative cleavage of the double bond.

Question 8

Which sequence of reagents would convert cyclohexene to adipic dialdehyde ($$OHC-(CH_2$)_4-CHO$$)?

Accepted Answer

$$O_3$$ followed by $$H_2O$$

Question 9

A chemist wants to synthesize 1,2-cyclohexanediol from cyclohexene. Which reagent should be used?

Accepted Answer

$$OsO_4$$, $$NMO$$, acetone, $$H_2O$$

Question 10

Which of the following is the correct synthetic route to convert 4-methoxy-1-phenylbut-1-ene to 1,4-benzenediol and 4-methoxyphenol?

Accepted Answer

Oxidative cleavage with $$O_3$$ followed by $$H_2O$$

Question 11

What is the major product when 1,2-dimethylcyclohexene is treated with $$O_3$$ followed by $$H_2O$$?

Accepted Answer

Two carboxylic acids formed by oxidative cleavage.

Question 12

Which of the following reagents would convert cyclopentene to cyclopentene oxide?

Accepted Answer

$$m-$$CPBA$

Question 13

A student wants to convert 1-bromo-2-methyl-2-propanol to 2-methyl-2-propanol. Which reagent should be used?

Accepted Answer

$$HBr$$

Question 14

Which of the following best describes the product of ozonolysis of 1,2-dimethylcyclohexene followed by $$Me_2S$$?

Accepted Answer

Two ketones.

Question 15

What is the expected product when 1,2-dimethylcyclohexene is treated with $$O_3$$ followed by $$H_2O$$?

Accepted Answer

Two carboxylic acids.

Question 16

Which of the following reagents would convert cyclohexene to adipic acid?

Accepted Answer

$$O_3$$ followed by $$H_2O$$

Question 17

A chemist wants to synthesize 1,2-cyclohexanediol from cyclohexene. Which reagent should be used?

Accepted Answer

$$OsO_4$$, $$NMO$$, acetone, $$H_2O$$

Question 18

Which of the following is the correct synthetic route to convert 4-methoxy-1-phenylbut-1-ene to 1,4-benzenediol and 4-methoxyphenol?

Accepted Answer

Oxidative cleavage with $$O_3$$ followed by $$H_2O$$

Organic Chemistry: Practice Worksheet on Reaction Mechanisms and Synthesis

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