Deck 22: Phenols

Question 1

Arrange the following three compounds in order of increasing acidity.

A) I $<$ II $<$ III
B) I $<$ III $<$ II
C) II $<$ III $<$ I
D) III $<$ I $<$ II

Answer 1

I $<$ III $<$ II

Question 2

What is the product of the following reaction?

A)

B)

C)

D)

Answer 2

Question 3

Arrange the following in order of decreasing acidity.
I. phenol
II. m-nitrophenol
III. $p$ -nitrophenol

A) III $>$ I $>$ II
B) III $>$ II $>$ I
C) II $>$ I $>$ III
D) II $>$ III $>$ I

Answer 3

III $>$ II $>$ I

Question 4

What is the product of the following reaction?

A)

B)

C)
D)

Question 5

Indicate where the isotopically labeled carbon atom $\left({ }^{*}\right)$ is located in the product.

A) $\# 1$
B) $\# 2$
C) $\# 3$
D) equally distributed between $\# 1$ and $\# 2$

Question 6

Identify the reagent(s) needed to carry out the following conversion.

A) Na metal
B) $\mathrm{LiAlH}_{4}$
C) $\mathrm{Na}_{2} \mathrm{Cr}_{2} \mathrm{O}_{7}, \mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{H}_{2} \mathrm{O}$
D) $\mathrm{NaOH}$

Question 7

Which of the following are the products of the reaction shown below?

A) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}$ and meta-bromophenol
B) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}$ and meta-bromophenol
C) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCl}$ and meta-bromochlorobenzene
D) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}$ and meta-bromochlorobenzene

Question 8

Which of the following methods works best to synthesize the compound shown below?

A)

B)

C)

D)

Question 9

Which of the following is the Claisen rearrangement product from the reaction below?

A)

B)

C)

D)

Question 10

Which structure is most consistent with the ${ }^{1} \mathrm{H}$ NMR spectrum below?

A)

B)

C)

D)

Question 11

Which structure would be consistent with the ${ }^{13} \mathrm{C}$ NMR shown?

A)

B)

C)

D)