Question 1

Which of the following best describes the functional group present in all alcohols?

Accepted Answer

A hydroxy group attached to an sp$$^{3}$$ hybridized carbon

Question 2

When naming an alcohol according to IUPAC rules, which of the following steps is performed first?

Accepted Answer

Find the longest carbon chain containing the hydroxy group

Question 3

What is the correct IUPAC name for the following structure?

$$
\begin{array}{c}
	ext{CH}_3-CH_2-CH(OH)-CH_2-CH_3
\end{array}
$$

Accepted Answer

3-pentanol

Question 4

Which of the following statements about the acidity of phenol compared to cyclohexanol is correct?

Accepted Answer

Phenol is more acidic because its conjugate base is stabilized by resonance

Question 5

Which reagent is most appropriate for the complete reduction of a carboxylic acid to a primary alcohol?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$

Question 6

What is the product of the following reaction?

$$
	ext{Cyclohexanone} + \mathrm{NaBH_4} \xrightarrow{	ext{EtOH}} ?
$$

Accepted Answer

Cyclohexanol

Question 7

Which of the following bases is strong enough to deprotonate an alcohol?

Accepted Answer

$$\mathrm{$$NaNH_2$$}$$

Question 8

Which of the following is the correct order of acidity (most to least acidic)?

Accepted Answer

Phenol \u003e Cyclohexanol \u003e Ethanol

Question 9

What is the oxidation number of carbon in methanol ($$\mathrm{CH_3OH}$$)?

Accepted Answer

$$-2$$

Question 10

Which of the following reactions will convert a secondary alcohol to a ketone?

Accepted Answer

Oxidation with $$\mathrm{PCC}$$

Question 11

Which of the following is a correct statement about the protection of alcohols in organic synthesis?

Accepted Answer

Alcohols are protected by converting them to silyl ethers using $$\mathrm{TMSCl}$$

Question 12

Which of the following best explains why the p$$K_a of $$phenol is much lower than that of cyclohexanol?

Accepted Answer

Phenol's conjugate base is stabilized by resonance

Question 13

Which of the following is the correct product for the reaction of 1-bromopropane with $$\mathrm{Mg} in $$ether followed by addition to acetone and acidic workup?

Accepted Answer

2-pentanol

Question 14

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

Accepted Answer

Primary alcohols can be oxidized to aldehydes using $$\mathrm{PCC}$$

Question 15

Which of the following is the correct mechanism for the reaction of a Grignard reagent with a ketone?

Accepted Answer

Nucleophilic addition to the carbonyl carbon followed by protonation

Question 16

Which of the following is a correct statement about the reactivity of $$\mathrm{$$LiAlH_4$$}$$ and $$\mathrm{$$NaBH_4$$}$$?

Accepted Answer

$$\mathrm{$$LiAlH_4$$} is $$more reactive and can reduce esters

Question 17

Which of the following is the correct IUPAC name for a cyclopentane ring with a hydroxy group and two methyl groups at positions 3 and 3?

Accepted Answer

(R)-3,3-dimethylcyclopentanol

Question 18

Which of the following is the best method to convert a primary alkyl halide to a primary alcohol?

Accepted Answer

React with $$\mathrm{NaOH}$$ via an $$\mathrm{S_N2}$$ mechanism

Question 19

Which of the following statements about the Markovnikov addition of water to an alkene is correct?

Accepted Answer

The hydroxy group adds to the more substituted carbon

Alcohols: Structure, Nomenclature, Acidity, Synthesis, and Reactions

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