Question 1

Which of the following is the major product when 1-methylcyclohexene is treated with $$\mathrm{H_2O}$$ and $$\mathrm{H_2SO_4}$$ under standard conditions?

Accepted Answer

1-methylcyclohexanol (Markovnikov addition at the double bond)

Question 2

What is the expected stereochemistry of the product when 1,2-dimethylcyclohexene is treated with $$\mathrm{Br_2$} in$$ $$\mathrm{CH_2Cl_2}$$?

Accepted Answer

Trans-1,2-dibromo-1,2-dimethylcyclohexane (anti addition)

Question 3

Which reagent would you use to convert cyclohexene to cyclohexane?

Accepted Answer

$$\mathrm{H_2$}$$, $$\mathrm{Pd/C}$$

Question 4

What is the major product when 1-bromo-2-methylpropane is treated with $$\mathrm{$$NaOCH_3$$}$$?

Accepted Answer

2-methylpropene (via E2 elimination)

Question 5

Which of the following is the correct product when cyclohexene is treated with $$\mathrm{$$KMnO_4$$}$$ and heat?

Accepted Answer

Adipic acid ($$\mathrm{HOOC-(CH_2$)_4-COOH})$$

Question 6

In the synthetic scheme converting 2-methyl-2-butene to 2,3-dimethyl-2-butene, which reagent is most appropriate for the final step?

Accepted Answer

$$\mathrm{KOH}$$, heat (E2 elimination)

Question 7

Which sequence of reagents would best convert cyclohexyl bromide to 1,3-cyclohexadiene?

Accepted Answer

1) $$\mathrm{$$NaNH_2$$}$$, 2) heat

Question 8

During ozonolysis of cyclohexene followed by reductive workup with dimethyl sulfide, what is the major organic product?

Accepted Answer

Adipaldehyde ($$\mathrm{OHC-(CH_2$)_4-CHO})$$

Question 9

In the ozonolysis reaction of cyclohexene, what is the role of dimethyl sulfide ($$\mathrm{Me_2S}$$)?

Accepted Answer

It acts as a reducing agent to convert ozonides to aldehydes

Question 10

Which of the following best describes the mechanism for the E2 elimination of 1-bromo-2-methylpropane with $$\mathrm{$$NaOCH_3$$}$$?

Accepted Answer

Concerted removal of a proton and bromide, forming a double bond

Question 11

Which product is formed when 1,2-dimethylcyclohexene is treated with $$\mathrm{Br_2$} in$$ $$\mathrm{CH_2Cl_2}$$, and what is the stereochemistry?

Accepted Answer

Trans-1,2-dibromo-1,2-dimethylcyclohexane (anti addition)

Question 12

What is the missing intermediate in the following synthetic scheme: $$\mathrm{2-methyl-2-butene \xrightarrow{Br_2$} ? \xrightarrow{KOH, heat} 2,3-dimethyl-2-butene}$$?

Accepted Answer

2,3-dibromo-2-methylbutane

Question 13

Which of the following is a byproduct of the ozonolysis of cyclohexene with dimethyl sulfide workup?

Accepted Answer

Dimethyl sulfoxide ($$\mathrm{Me_2SO})$$

Question 14

Which of the following best describes the regiochemistry of acid-catalyzed hydration of 1-methylcyclohexene?

Accepted Answer

Markovnikov addition: OH adds to the more substituted carbon

Question 15

Which of the following is the correct arrow-pushing mechanism for the ozonolysis of cyclohexene under reductive conditions?

Accepted Answer

Formation of molozonide, rearrangement to ozonide, reduction to dialdehyde

Question 16

Which synthetic route would best convert cyclohexyl bromide to 1,3-cyclohexadiene?

Accepted Answer

Double E2 elimination using $$\mathrm{$$NaNH_2$$}$$ and heat

Question 17

What is the major product when cyclohexene is treated with hot, concentrated $$\mathrm{$$KMnO_4$$}$$?

Accepted Answer

Adipic acid ($$\mathrm{HOOC-(CH_2$)_4-COOH})$$

Question 18

Which of the following is the correct product when 1-bromo-2-methylpropane is treated with $$\mathrm{$$NaOCH_3$$}$$?

Accepted Answer

2-methylpropene (via E2 elimination)

Question 19

Which of the following is the correct product when cyclohexene is treated with $$\mathrm{H_2$}$$ and $$\mathrm{Pd/C}$$?

Accepted Answer

Cyclohexane

Organic Chemistry: Reaction Mechanisms, Synthesis, and Stereochemistry Study Guide

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