Question 1

Which of the following is the correct IUPAC name for the compound shown below?

$$\mathrm{\begin{array}{c}
\chemfig{*6(---(-OH)--)}
\end{array}}$$

Accepted Answer

Cyclohexanol

Question 2

Alcohols are named by adding which modifier to the end of the parent alkane name?

Accepted Answer

-ol

Question 3

Which of the following alcohols is classified as a diol?

Accepted Answer

Ethylene glycol ($$\mathrm{HOCH_2CH_2OH})$$

Question 4

Phenols are more acidic than typical alcohols due to which effect?

Accepted Answer

Resonance effect

Question 5

Which substituent will make phenol most acidic?

Accepted Answer

A nitro group ($$\mathrm{-NO_2$}) at $$the para position

Question 6

Rank the following phenols in order of increasing acidity: phenol, p-nitrophenol, p-methylphenol.

Accepted Answer

p-methylphenol \u003c phenol \u003c p-nitrophenol

Question 7

Which of the following is a correct general mechanism for nucleophilic addition to a carbonyl compound?

Accepted Answer

$$\mathrm{R_2C=O + Nu^- \rightarrow R_2C(OH)Nu}$$

Question 8

Which reagent would you use to synthesize a primary alcohol from an aldehyde?

Accepted Answer

NaBH$$_4$$

Question 9

Which of the following statements about Grignard reagents is correct?

Accepted Answer

They are strong nucleophiles and react with carbonyl compounds to form alcohols.

Question 10

What is the product of the following reaction?

$$\mathrm{CH_3COCH_3 + $$LiAlH_4$$ \rightarrow}$$

Accepted Answer

$$\mathrm{(CH_3$)_2CHOH}$$

Question 11

Which of the following best describes the oxidation of a sulfide?

Accepted Answer

Increase in the number of bonds to oxygen

Question 12

Which of the following is the correct IUPAC name for $$\mathrm{CH_3CH_2SH}$$?

Accepted Answer

Ethanethiol

Question 13

Which of the following is a correct statement about thiols?

Accepted Answer

They contain a sulfur analog of the hydroxyl group.

Question 14

Which of the following transformations is an example of reduction?

Accepted Answer

$$\mathrm{CH_3COCH_3 \rightarrow (CH_3$)_2CHOH}$$

Question 15

Which of the following is the best method to synthesize 2-propanol from acetone?

Accepted Answer

Reduction with NaBH$$_4$$

Question 16

Which of the following is a product of the reaction of a Grignard reagent with formaldehyde followed by acid workup?

Accepted Answer

A primary alcohol

Question 17

Which of the following is the correct order of increasing acidity for the following compounds: phenol, p-methoxyphenol, p-nitrophenol?

Accepted Answer

p-methoxyphenol \u003c phenol \u003c p-nitrophenol

Question 18

Which of the following statements about the oxidation of alcohols is correct?

Accepted Answer

Primary alcohols can be oxidized to aldehydes and then to carboxylic acids.

Question 19

Which of the following is the product of the reaction of 1-bromopropane with Mg in ether, followed by reaction with acetone and acid workup?

Accepted Answer

2-methyl-2-pentanol

Structure and Synthesis of Alcohols: Nomenclature, Acidity, Synthesis, and Related Sulfur Compounds

Study Guide - Practice Questions