Q: A student treats 2-methylpropene with Br$_2$ in water. What is the major organic product?

$$ \text{1-bromo-2-methylpropan-1-ol} $$

Q: What is the product of the following reaction sequence? $$ \text{Cyclohexene} \xrightarrow{1. \text{OsO}_4} \xrightarrow{2. \text{H}_2\text{S}} $$

$$ \text{cis-1,2-cyclohexanediol} $$

Q: Which reagent would convert a primary alcohol to a carboxylic acid?

$$ \text{Jones reagent (CrO}_3, \text{H}_2\text{SO}_4) $$

Q: A student wants to synthesize ethyl propyl ether from 1-bromopropane and ethanol. Which sequence of reagents would be most effective?

$$ \text{NaOEt, 1-bromopropane} $$

Q: Which of the following transformations would result in a racemic mixture?

$$ \text{Addition of HBr to 2-methyl-2-butene} $$

Q: Which of the following best explains why PCC is preferred over Jones reagent for oxidizing a primary alcohol to an aldehyde?

$$ \text{PCC does not over-oxidize to carboxylic acid} $$

Q: Which of the following statements about the reaction of cyclohexanol with H$_2$SO$_4$ is correct?

$$ \text{It produces cyclohexene via dehydration} $$

Q: Which of the following best describes the product of the reaction of 1-methylcyclohexanol with HBr?

$$ \text{1-bromo-1-methylcyclohexane} $$

Q: Which of the following reactions would result in anti addition of substituents across a double bond?

$$ \text{Br}_2 \text{ addition to cyclohexene} $$

Q: Which of the following is the correct product for the reaction of cyclohexene with Br$_2$ in CCl$_4$?

$$ \text{trans-1,2-dibromocyclohexane} $$

Question 1

Which of the following sets of reagents would best accomplish the transformation of cyclohexanol to cyclohexanone?

Accepted Answer

$$ 	ext{PCC} $$

Question 2

A student treats 2-methylpropene with Br$_2$ in water. What is the major organic product?

Accepted Answer

$$ 	ext{1-bromo-2-methylpropan-1-ol} $$

Question 3

Which of the following molecules would show only one $^1$H NMR signal?

Accepted Answer

$$ 	ext{Cyclohexane} $$

Question 4

What is the product of the following reaction sequence?

$$ 	ext{Cyclohexene} \xrightarrow{1. 	ext{OsO}_4} \xrightarrow{2. 	ext{H}_2	ext{S}} $$

Accepted Answer

$$ 	ext{cis-1,2-cyclohexanediol} $$

Question 5

Which of the following best describes the mechanism for the reaction of 2-butanol with HBr to give 2-bromobutane?

Accepted Answer

$$ 	ext{SN1 substitution} $$

Question 6

How many unique $^1$H NMR signals would be observed for 2,2-dimethylpropane?

Accepted Answer

$$ 1 $$

Question 7

Which reagent would convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$ 	ext{Jones reagent (CrO}_3, 	ext{H}_2	ext{SO}_4) $$

Question 8

A student wants to synthesize ethyl propyl ether from 1-bromopropane and ethanol. Which sequence of reagents would be most effective?

Accepted Answer

$$ 	ext{NaOEt, 1-bromopropane} $$

Question 9

Which of the following transformations would result in a racemic mixture?

Accepted Answer

$$ 	ext{Addition of HBr to 2-methyl-2-butene} $$

Question 10

Which of the following best explains why PCC is preferred over Jones reagent for oxidizing a primary alcohol to an aldehyde?

Accepted Answer

$$ 	ext{PCC does not over-oxidize to carboxylic acid} $$

Question 11

Which of the following statements about the reaction of cyclohexanol with H$_2$SO$_4$ is correct?

Accepted Answer

$$ 	ext{It produces cyclohexene via dehydration} $$

Question 12

Which of the following is the best reagent to convert a secondary alcohol to a ketone?

Accepted Answer

$$ 	ext{PCC} $$

Question 13

Which of the following best describes the product of the reaction of 1-methylcyclohexanol with HBr?

Accepted Answer

$$ 	ext{1-bromo-1-methylcyclohexane} $$

Question 14

Which of the following is the correct IUPAC name for the molecule shown below?

(CH$_3$)$_2$CHCH$_2$CH$_2$CH$_3$

Accepted Answer

$$ 	ext{3-methylpentane} $$

Question 15

Which of the following reactions would result in anti addition of substituents across a double bond?

Accepted Answer

$$ 	ext{Br}_2 	ext{ addition to cyclohexene} $$

Question 16

Which of the following best describes the product of the reaction of 1-bromopropane with NaOEt?

Accepted Answer

$$ 	ext{1-ethoxypropane} $$

Question 17

Which of the following is the correct product for the reaction of cyclohexene with Br$_2$ in CCl$_4$?

Accepted Answer

$$ 	ext{trans-1,2-dibromocyclohexane} $$

Question 18

Which of the following best explains why the reaction of 2-methyl-2-butene with HBr produces a racemic mixture?

Accepted Answer

$$ 	ext{The reaction proceeds via a planar carbocation intermediate} $$

Question 19

Which of the following is the best method to synthesize 1-bromocyclohexane from cyclohexanol?

Accepted Answer

$$ 	ext{PBr}_3 $$

Organic Chemistry Exam Study Guide: Structure, Reactions, and Spectroscopy

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