Question 1

Which of the following statements best explains why phenols are more acidic than alcohols?

Accepted Answer

Phenols undergo resonance stabilization of their conjugate base.

Question 2

What is the product of the following reaction? $$CH_3CH_2Br + Mg \xrightarrow{Et_2O} $$

Accepted Answer

$$CH_3CH_2MgBr$$

Question 3

Which reagent is most suitable for the reduction of esters to alcohols?

Accepted Answer

$$LiAlH_4$$

Question 4

In the Williamson ether synthesis, which of the following combinations will result in the formation of an ether?

Accepted Answer

A primary alkyl halide and sodium alkoxide

Question 5

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

$$CH_3CH_2CH(OH)CH_2CH_3$$

Accepted Answer

2-pentanol

Question 6

Why do alcohols generally have higher boiling points than alkanes of similar molecular weight?

Accepted Answer

Alcohols have stronger hydrogen bonding interactions.

Question 7

Which of the following statements about Grignard reagents is TRUE?

Accepted Answer

Grignard reagents are strong bases and react rapidly with protic solvents.

Question 8

Which of the following reactions will NOT occur with a Grignard reagent?

Accepted Answer

SN2 reaction with a secondary alkyl halide

Question 9

What is the major product when $$CH_3CH_2MgBr$$ reacts with $$CH_3COCH_3$$ followed by acidic workup?

Accepted Answer

$$(CH_3$)_2C(OH)CH_2CH_3$$

Question 10

Which of the following best describes the role of sodium borohydride ($$NaBH_4) in $$organic synthesis?

Accepted Answer

It reduces aldehydes and ketones to alcohols.

Question 11

Which of the following is a correct statement about the acidity of alcohols and phenols?

Accepted Answer

Phenols are more acidic than alcohols because their conjugate base is resonance stabilized.

Question 12

Which of the following statements about the reaction of Grignard reagents with esters is correct?

Accepted Answer

Grignard reagents react with esters to give tertiary alcohols after two additions.

Question 13

Which of the following is the correct product of the reduction of cyclohexanone with $$NaBH_4$$?

Accepted Answer

Cyclohexanol

Question 14

Which of the following is the correct order of reactivity for halides in the formation of Grignard reagents?

Accepted Answer

$$I \u003e Br \u003e Cl \u003e F$$

Question 15

Which of the following statements about the reduction of esters with $$NaBH_4$$ and $$LiAlH_4 is $$correct?

Accepted Answer

$$LiAlH_4$$ reduces esters to alcohols, but $$NaBH_4$$ does not.

Question 16

Which of the following is the correct mechanism for the reduction of a ketone with $$NaBH_4$$?

Accepted Answer

Hydride addition to the carbonyl carbon followed by protonation.

Question 17

Which of the following statements about the use of deuterium in Grignard reactions is correct?

Accepted Answer

Deuterium can be introduced by reacting a Grignard reagent with $$D_2O.$$

Question 18

Which of the following is the correct product when $$PhMgBr ($$phenylmagnesium bromide) reacts with $$CO_2$$ followed by acidic workup?

Accepted Answer

Benzoic acid

Question 19

Which of the following statements about the reactivity of Grignard reagents is correct?

Accepted Answer

Grignard reagents react faster with terminal alkynes than with carbonyl compounds.

Structure and Synthesis of Alcohols (Chapter 10): Study Notes

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