Question 1

What is the IUPAC name for the compound shown below?

$$\begin{array}{c}
	ext{(Image 1)}
\end{array}$$

Accepted Answer

2,2-dimethylpropanal

Question 2

Which of the following structures corresponds to benzophenone?

$$\begin{array}{c}
	ext{(Image 2)}
\end{array}$$

Accepted Answer

B

Question 3

What is the IUPAC name for the following compound?

$$\begin{array}{c}
	ext{(Image 3)}
\end{array}$$

Accepted Answer

N-methyl 3-methylhexanamide

Question 4

Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except:

Accepted Answer

Aqueous acid

Question 5

Which of the following substrates cannot be used as an immediate precursor to synthesize an ester?

$$\begin{array}{c}
	ext{(Image 4)}
\end{array}$$

Accepted Answer

B

Question 6

Using $$^1H $$NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?

Accepted Answer

An aldehyde has a proton signal between 9–10 ppm.

Question 7

Is the following reaction reversible and, if so, under what conditions?

$$\begin{array}{c}
	ext{(Image 5)}
\end{array}$$

Accepted Answer

Yes, under acidic conditions

Question 8

Why are strongly acidic conditions not used in the formation of enamines and imines?

Accepted Answer

The amine will be completely protonated.

Question 9

In which compound does the carbonyl group absorb at the lowest frequency in the Infrared spectrum?

$$\begin{array}{c}
	ext{(Image 6)}
\end{array}$$

Accepted Answer

B

Question 10

Select the structure of the product in the following reaction:

$$\begin{array}{c}
	ext{(Image 7)}
\end{array}$$
$$\begin{array}{c}
	ext{(Image 8)}
\end{array}$$

Accepted Answer

D

Question 11

Which reagent(s) would you use to prepare the following ylide from the phosphonium salt in the reaction shown below?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2^-Li} ($$nBu–Li)

Question 12

Why is pyridine included as a reagent in the reaction of an acid chloride and an amine or alcohol?

Accepted Answer

Pyridine will neutralize the acid by-product of the reaction.

Question 13

Which of the following reaction pathways could be used to convert a carboxylic acid into an ester?

Accepted Answer

1 and 3

Question 14

What is the immediate product for the following reaction?

$$\begin{array}{c}
	ext{(Image 9)}
\end{array}$$

Accepted Answer

A cyanohydrin

Question 15

Select the structure of the product of the following reaction:

$$\begin{array}{c}
	ext{(Image 10)}
\end{array}$$

Accepted Answer

D

Question 16

Rank the following compounds in order of increasing reactivity in nucleophilic substitution:

$$\begin{array}{c}
	ext{(Image 11)}
\end{array}$$

Accepted Answer

2 \u003c 3 \u003c 1

Question 17

Which of the following is the direct product of the base-promoted hydrolysis of an ester?

Accepted Answer

A carboxylate salt

Question 18

Select the structure of the product of the following reaction:

$$\begin{array}{c}
	ext{(Image 12)}
\end{array}$$
$$\begin{array}{c}
	ext{(Image 13)}
\end{array}$$

Accepted Answer

D

Question 19

Select the product of the following reaction:

$$\begin{array}{c}
	ext{(Image 14)}
\end{array}$$

Accepted Answer

Hexylamine

Question 20

The structure below is $$\alpha-D-$$galactose.

$$\begin{array}{c}
	ext{(Image 15)}
\end{array}$$
Identify the hemiacetal carbon atom in this structure.

Accepted Answer

A

Question 21

Select the structure for the compound whose IUPAC name is pentyl 2-methylbutanoate.

$$\begin{array}{c}
	ext{(Image 16)}
\end{array}$$

Accepted Answer

C

Organic Chemistry Practice Exam 3 – Step-by-Step Guidance

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