Question 1

Which of the following compounds are ethers? (Refer to the first image with four structures labeled 1-4.)

Accepted Answer

1, 2, 3 and 4

Question 2

What is the IUPAC name of the compound shown in the second image (phenyl group attached to a butanal)?

Accepted Answer

3-phenylbutanal

Question 3

In the reaction of benzaldehyde with HCN (see third image), what is the major organic product?

Accepted Answer

2-hydroxy-2-phenylacetonitrile

Question 4

In the reaction of phenylbutanal with HC≡C–Cu followed by H2O (see fourth image), what is the major organic product?

Accepted Answer

PhCH2CH(OH)C≡CH

Question 5

What is the major organic product obtained from the acid-catalyzed cyclization of 5-hydroxyhexanal (see fifth image)?

Accepted Answer

2-methyltetrahydrofuran-3-ol

Question 6

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

Accepted Answer

di-tert-butyl ether

Question 7

What type of reactive intermediate is formed in the reaction of 2-ethoxy-2-methylbutane with HBr to give 2-ethoxy-2-methylbutyl bromide?

Accepted Answer

2-methylbutyl cation

Question 8

What is the intermediate in the Sandmeyer reaction (see eighth image)?

Accepted Answer

an aryldiazonium salt

Question 9

Which of the following amines can be prepared by ring opening of an epoxide with sodium amide followed by reduction?

Accepted Answer

only 1 and 4

Question 10

What is the best choice of reagent(s) to perform the following transformation: alkene to alcohol (see study materials)?

Accepted Answer

H2O, H2SO4

Question 11

Which of the following statements is true regarding nucleophilic addition to carbonyl groups?

Accepted Answer

Nucleophilic addition to carbonyl groups can be catalyzed by acid or base

Question 12

Which of the following statements is NOT true about the Wittig reaction?

Accepted Answer

Reaction of propanal with methanol in the presence of base gives an acetal

Question 13

What is the major organic product obtained from the reaction of methyl epoxide with water and acid (see twelfth image)?

Accepted Answer

$$\mathrm{CH_3CH(OH)CH_2OH}$$

Question 14

What is the major organic product obtained from the reaction of methyl epoxide with sodium methoxide in methanol (see thirteenth image)?

Accepted Answer

$$\mathrm{CH_3CH(OH)CH_2OCH_3}$$

Question 15

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare a tertiary alcohol by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

Accepted Answer

only 2 and 3

Question 16

Which of the following is the weakest base among the amines listed?

Accepted Answer

4-methoxy-m-phenylenediamine

Question 17

Which of the following is the strongest base among the amines listed?

Accepted Answer

triethylamine

Question 18

What is the major organic product obtained from the following sequence of reactions: nitration, reduction, diazotization, and Sandmeyer cyanation of p-toluene (see tenth and eleventh images)?

Accepted Answer

p-tolyl cyanide

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