Q: Rank the following alkyl halides in order of increasing $$S_N1$$ reactivity (1 = least reactive, 4 = most reactive): $$\text{(i) tert-butyl chloride}$$ $$\text{(ii) isopropyl bromide}$$ $$\text{(iii) methyl chloride}$$ $$\text{(iv) benzyl chloride}$$

$$\text{(iii) \u003c (ii) \u003c (i) \u003c (iv)}$$

Q: Which of the following is the correct sequence of reagents to convert cyclobutanecarbaldehyde to 1-pentanol?

Grignard reagent ($$\text{CH}_3\text{MgBr}$$), then $$\text{H}_2\text{O}$$

Question 1

Which of the following functional groups is NOT present in the structure of levonorgestrel, a synthetic progestin used in hormone replacement therapy?

Accepted Answer

Amide

Question 2

Rank the following alkyl halides in order of increasing $$S_N1$$ reactivity (1 = least reactive, 4 = most reactive):

$$	ext{(i) tert-butyl chloride}$$ 
$$	ext{(ii) isopropyl bromide}$$ 
$$	ext{(iii) methyl chloride}$$ 
$$	ext{(iv) benzyl chloride}$$

Accepted Answer

$$	ext{(iii) \u003c (ii) \u003c (i) \u003c (iv)}$$

Question 3

Which of the following alkenes is the most stable?

Accepted Answer

1,2-dimethylcyclopentene

Question 4

What is the correct IUPAC name for the following compound:

A six-carbon chain with a fluorine on carbon 4 and a hydroxyl group on carbon 2, with the double bond between carbons 3 and 4 in the E configuration.

Accepted Answer

(E)-4-Fluoro-2-Hexen-1-ol

Question 5

Which reagent sequence would convert 1-butanol to 1-bromobutane?

Accepted Answer

$$	ext{PBr}_3$$

Question 6

A cyclohexanol is oxidized to cyclohexanone. Which reagent is most appropriate for this transformation?

Accepted Answer

$$	ext{PCC}$$

Question 7

Which of the following is the major product when 1-bromo-2,2-dimethylcyclohexane is treated with aqueous $$	ext{NaOH}$$?

Accepted Answer

2,2-dimethylcyclohexanol

Question 8

Which of the following reaction sequences would best convert cyclopentanol to cyclopentyl chloride?

Accepted Answer

SOCl$$_2$$ only

Question 9

Which of the following is the correct product of the reaction of 4-bromoanisole with NaOH and heat?

Accepted Answer

4-methoxyphenol

Question 10

Which of the following is the correct sequence of reagents to convert cyclobutanecarbaldehyde to 1-pentanol?

Accepted Answer

Grignard reagent ($$	ext{CH}_3	ext{MgBr}$$), then $$	ext{H}_2	ext{O}$$

Question 11

Which of the following is the best method to synthesize cyclopentylacetonitrile from cyclopentane and ethyl bromide?

Accepted Answer

Alkylation of cyclopentyl bromide with NaCN

Question 12

In the reaction of tert-butyl bromide with methanol, what is the major product?

Accepted Answer

tert-butyl methyl ether

Question 13

Which of the following best explains why benzyl chloride is more reactive in $$S_N1$$ reactions than methyl chloride?

Accepted Answer

Benzyl chloride forms a resonance-stabilized carbocation

Question 14

Which of the following is the correct order of increasing alkene stability?

Accepted Answer

Monosubstituted \u003c Disubstituted \u003c Trisubstituted \u003c Tetrasubstituted

Question 15

Which of the following reagents would convert a primary alcohol to a tosylate?

Accepted Answer

TsCl, pyridine

Question 16

Which of the following is the major product when 1-bromo-2,2-dimethylcyclohexane is treated with methanol?

Accepted Answer

2,2-dimethylcyclohexyl methyl ether

Question 17

Which of the following is the correct product of the reaction of cyclohexyl bromide with aqueous NaOH?

Accepted Answer

Cyclohexanol

Question 18

Which of the following is the correct product of the reaction of 4-bromoanisole with NaOH and heat?

Accepted Answer

4-methoxyphenol

Question 19

Which of the following is the correct product of the reaction of cyclobutanecarbaldehyde with methylmagnesium bromide followed by water?

Accepted Answer

1-pentanol

Organic Chemistry: Functional Groups, Reactivity, Synthesis, and Mechanisms Study Guide

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