Deck 15: Alcohols, Diols, and Thiols

Question 1

What is the product of the following reactions?

A) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$
B) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
C) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}$
D) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Answer 1

$\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$

Question 2

Which of the following cannot be made by the reduction of a ketone or aldehyde with $\mathrm{NaBH}_{4}$ in methanol?

A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol

Answer 2

2-methyl-2-propanol

Question 3

What is the product of the following reaction?

A) A
B) B
C) C
D) D

Answer 3

C

Question 4

Give the product of the following reaction.

A) A
B) B
C) C
D) D

Question 5

The reaction of a Grignard reagent with ethylene oxide followed by dilute acid gives

A) a primary alcohol.
B) a secondary alcohol.
C) a tertiary alcohol.
D) methanol.

Question 6

Consider the conversion of 1-butanol to each of the compounds shown below. In which conversion is an oxidizing agent needed?

A) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}$
B) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$
C) $\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2} \mathrm{O}$
D) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{O}$

Question 7

Which of the following syntheses gives 3-methyl-1-hexanol?

A)

B)

C)

D)

Question 8

What is the product of the synthetic sequence below?

A)

B)

C)

D)

Question 9

Compound $\mathrm{A}, \mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}$ , is readily oxidized with $\mathrm{K}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}$ in $\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{H}_{2} \mathrm{O}$ to give compound $\mathrm{B}, \mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}$ . Compound $\mathrm{B}$ has four peaks in its C-13 NMR (broadband decoupled). Which one of the following fits the data for compound $\mathrm{A}$ ?

A) A
B) B
C) C
D) D

Question 10

What is the final product of the following reactions?

A) 2,3-dimethyl-3-pentanol
B) 2,3-dimethyl-2-pentanol
C) 2,4-dimethyl-3-pentanol
D) 2,2-dimethyl-3-pentanol

Question 11

What is the product of the reaction below?

A)

B)

C)

D)

Question 12

What is the product of the following reaction sequence?

A) A
B) B
C) C
D) D

Question 13

Which one of the following reaction steps work best to carry out the transformation shown below?

A)

B)

C)

D)

Question 14

What is the product of the following reaction sequence?
Cyclopentanone $\xrightarrow[\mathrm{CH}_{3} \mathrm{OH}]{\mathrm{NaBH}_{4}} \xrightarrow[\text { heat }]{\mathrm{H}_{2} \mathrm{SO}_{4}}$

A) cyclopentene oxide
B) cyclopentene
C) cyclopentane
D) cis-1,2-cyclopentanediol

Question 15

To which side, if any, would the reaction below lie?

A) to the right
B) to the left
C) equally to both sides
D) this reaction cannot occur