Q: In the Williamson ether synthesis, which combination of reactants would maximize the yield of ethyl methyl ether?

Reacting methyl bromide with sodium ethoxide

Q: Which of the following best describes the stereochemical outcome when an epoxide is opened by a nucleophile under basic conditions?

The nucleophile attacks the less substituted carbon with inversion of configuration

Q: Which of the following best describes the product(s) when 1,2-dimethylcyclohexene is treated with $\mathrm{Br_2}$ in water?

A racemic mixture of bromohydrins

Q: Which of the following sequences would convert cyclohexyl bromide to cyclohexylacetylene?

1. $\mathrm{NaNH_2}$, 2. $\mathrm{CH_3I}$, 3. $\mathrm{NaNH_2}$

Q: Which of the following is the correct pKa order for the following acids: water, alcohol, carboxylic acid?

carboxylic acid < water < alcohol

Q: Which of the following best describes the product when cyclohexanol is treated with HCl?

A racemic mixture of cyclohexyl chloride

Question 1

Which of the following reagents would convert an epoxide to a trans-1,2-diol under basic conditions?

Accepted Answer

$\mathrm{NaOH,\ H_2O}$

Question 2

What is the major product when 2-methylcyclopentanol is treated with concentrated $\mathrm{H_2SO_4}$?

Accepted Answer

1,2-dimethylcyclopentene

Question 3

Which of the following best describes the mechanism for the acid-catalyzed conversion of hex-5-en-1-ol to a six-membered cyclic ether?

Accepted Answer

Intramolecular SN1 reaction after alcohol protonation

Question 4

Which of the following is the correct order of increasing acidity (lower to higher pKa) for the following functional groups: alcohol, alkyne, alkane?

Accepted Answer

alkane < alkyne < alcohol

Question 5

In the Williamson ether synthesis, which combination of reactants would maximize the yield of ethyl methyl ether?

Accepted Answer

Reacting methyl bromide with sodium ethoxide

Question 6

Which of the following best describes the stereochemical outcome when an epoxide is opened by a nucleophile under basic conditions?

Accepted Answer

The nucleophile attacks the less substituted carbon with inversion of configuration

Question 7

Which of the following reagents would convert 1-bromopentane to pentan-1-ol in a single step?

Accepted Answer

$\mathrm{NaOH}$

Question 8

Which of the following is the correct product when 1-bromo-2-methylpropane is treated with sodium methoxide?

Accepted Answer

1-methoxy-2-methylpropane

Question 9

Which of the following best describes the product(s) when 1,2-dimethylcyclohexene is treated with $\mathrm{Br_2}$ in water?

Accepted Answer

A racemic mixture of bromohydrins

Question 10

Which of the following sequences would convert cyclohexyl bromide to cyclohexylacetylene?

Accepted Answer

1. $\mathrm{NaNH_2}$, 2. $\mathrm{CH_3I}$, 3. $\mathrm{NaNH_2}$

Question 11

Which of the following is the correct product when 1-phenyl-2-propanol is treated with $\mathrm{NaOH}$?

Accepted Answer

1-phenyl-2-propanone

Question 12

Which of the following is the correct pKa order for the following acids: water, alcohol, carboxylic acid?

Accepted Answer

carboxylic acid < water < alcohol

Question 13

Which of the following best describes the product when cyclohexanol is treated with HCl?

Accepted Answer

A racemic mixture of cyclohexyl chloride

Question 14

Which of the following is the correct mechanism for the conversion of an alcohol to an alkene using $\mathrm{H_2SO_4}$?

Accepted Answer

E1 elimination

Question 15

Which of the following is the correct product when 1,2-dibromocyclohexane is treated with $\mathrm{NaNH_2}$?

Accepted Answer

Cyclohexyne

Question 16

Which of the following is the correct product when 1-chloro-2-methylpropene is treated with $\mathrm{NaOH}$?

Accepted Answer

2-methyl-2-propen-1-ol

Question 17

Which of the following is the correct product when 1,2-dibromopropane is treated with excess $\mathrm{NaNH_2}$?

Accepted Answer

Propyne

Question 18

Which of the following is the correct product when 1,2-epoxypropane is treated with $\mathrm{NaCN}$?

Accepted Answer

2-cyano-1-propanol

Stepwise Mechanism for Epoxide Ring Opening with Nucleophile

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