Question 1

Which of the following statements best explains why alcohols generally have higher boiling points than ethers of similar molecular weight?

Accepted Answer

Alcohols can form hydrogen bonds with each other, while ethers cannot.

Question 2

Which reagent would best convert 2-butanol to 2-bromobutane?

Accepted Answer

$$\mathrm{$$PBr_3$$}$$

Question 3

What is the major product when 1-methylcyclohexene reacts with water in the presence of dilute sulfuric acid?

Accepted Answer

1-methylcyclohexanol (Markovnikov addition)

Question 4

Which of the following best describes the mechanism of the Williamson ether synthesis?

Accepted Answer

An $$\mathrm{S_N2}$$ reaction between an alkoxide ion and a primary alkyl halide

Question 5

Which of the following alcohols will be most acidic?

Accepted Answer

2,4,6-trinitrophenol

Question 6

A student wants to synthesize 1-phenylethanol from acetophenone. Which reagent should they use?

Accepted Answer

$$\mathrm{$$NaBH_4$$}$$

Question 7

Which of the following statements about the Diels-Alder reaction is correct?

Accepted Answer

It is a concerted cycloaddition reaction between a conjugated diene and a dienophile.

Question 8

Which of the following is the best method to protect an alcohol group during a Grignard reaction?

Accepted Answer

Convert the alcohol to a silyl ether, such as a tert-butyldimethylsilyl (TBDMS) ether.

Question 9

Which of the following statements about the resonance stabilization of the allyl cation is correct?

Accepted Answer

The positive charge is delocalized over two carbon atoms, increasing stability.

Question 10

Which product is formed when 1,3-butadiene reacts with HBr at low temperature ($$-80^\circC$$)?

Accepted Answer

3-bromo-1-butene (1,2-addition product)

Question 11

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

Accepted Answer

Primary alcohols can be oxidized to aldehydes or carboxylic acids depending on the reagent.

Question 12

Which of the following best explains why crown ethers are useful in organic synthesis?

Accepted Answer

They solubilize metal cations in organic solvents, facilitating reactions such as nucleophilic substitutions.

Question 13

Which of the following is the correct order of reactivity of alcohols with hydrogen halides (HX) to form alkyl halides?

Accepted Answer

Tertiary $$\u003e$$ Secondary $$\u003e$$ Primary

Question 14

Which of the following statements about the reaction of epoxides with nucleophiles under basic conditions is correct?

Accepted Answer

The nucleophile attacks the less substituted carbon of the epoxide.

Question 15

Which of the following best describes the product of the reaction between a Grignard reagent ($$\mathrm{RMgBr}) $$and formaldehyde, followed by aqueous workup?

Accepted Answer

A primary alcohol

Question 16

Which of the following is a key feature of conjugated dienes compared to isolated dienes?

Accepted Answer

Conjugated dienes are more stable due to electron delocalization.

Question 17

Which of the following is the best method to synthesize an ether from an alcohol?

Accepted Answer

Convert the alcohol to an alkoxide and react with a primary alkyl halide (Williamson synthesis).

Question 18

Which of the following is the correct product of anti 1,2-dihydroxylation of an alkene via epoxide formation and subsequent acid-catalyzed hydrolysis?

Accepted Answer

A trans-1,2-diol

Question 19

Which of the following best describes the effect of electron-withdrawing groups on the acidity of phenols?

Accepted Answer

Electron-withdrawing groups increase the acidity by stabilizing the phenoxide ion.

Alcohols, Ethers, and Conjugated Unsaturated Systems: Structure, Synthesis, and Reactivity

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