Question 1

Which reagent would you use to selectively reduce an alkyne to a cis-alkene?

Accepted Answer

H\_2, Lindlar's catalyst

Question 2

What is the major organic product when 2-butyne is treated with excess HCl?

Accepted Answer

$$\mathrm{CH_3CHClCClCH_3}$$

Question 3

Which of the following best describes the nucleophile, electrophile, and leaving group in the reaction of 2-chlorobutane with NaOH?

Accepted Answer

Nucleophile: NaOH; Electrophile: 2-chlorobutane; Leaving group: Cl

Question 4

Rank the following cyclohexane derivatives from most to least stable: I (tert-butyl at axial), II (tert-butyl at equatorial), III (no tert-butyl).

Accepted Answer

II \u003e III \u003e I

Question 5

Which of the following is the major product of the E2 reaction of trans-1-bromo-4-methylcyclohexane with $$\mathrm{$$OCH_3$$^-}$$?

Accepted Answer

1-methylcyclohexene

Question 6

Which base would you use to favor the Hofmann product over the Zaitsev product in an E2 elimination?

Accepted Answer

Potassium tert-butoxide ($$\mathrm{KOtBu})$$

Question 7

What is the expected product when 1-hexyne is treated with 9-BBN followed by $$\mathrm{H_2O_2}$$ and $$\mathrm{NaOH}$$?

Accepted Answer

$$\mathrm{CH_3CH_2CH_2CH_2CH_2CHO}$$

Question 8

Which of the following ketones could NOT be prepared by acid-catalyzed hydration of an alkyne?

Accepted Answer

2,2-dimethyl-3-pentanone

Question 9

What is the correct order of reactivity for the following compounds in an $$\mathrm{S_N1}$$ reaction: I (1-bromopropane), II (cyclohexyl bromide), III (benzyl chloride), IV (allyl chloride)?

Accepted Answer

IV \u003e III \u003e II \u003e I

Question 10

Which of the following mechanisms correctly shows the curved arrows for the $$\mathrm{S_N2}$$ reaction of cyclohexyl chloride with $$\mathrm{NaCN}$$?

Accepted Answer

IV

Question 11

Which of the following is the major product when 1-bromocyclohexane is treated with $$\mathrm{$$OCH_3$$^-}$$?

Accepted Answer

Cyclohexene

Question 12

For the reaction of 2-bromopentane with $$\mathrm{CH_3O^-}$$, which product will be favored: Zaitsev or Hofmann?

Accepted Answer

Zaitsev product

Question 13

Which of the following best describes the hybridization of the carbons in acetylene ($$\mathrm{C_2H_2}$$)?

Accepted Answer

$$sp$$—$$sp$$

Question 14

What is the expected major product when 1-hexyne is treated with $$\mathrm{Na} in$$ $$\mathrm{NH_3$} ($$liq)?

Accepted Answer

trans-2-hexene

Question 15

Which of the following is the expected product when 1-hexyne is hydrogenated with $$\mathrm{H_2$}$$ and Pt?

Accepted Answer

hexane

Question 16

Which of the following is the correct product for the ozonolysis of 3-methyl-2-pentene?

Accepted Answer

$$\mathrm{CH_3COCH_2CH_3}$$ and $$\mathrm{CO_2$}$$

Question 17

Which of the following is the major product when 1-bromocyclohexane is treated with $$\mathrm{CH_3O^-} in a $$chair conformation?

Accepted Answer

The product formed by anti-periplanar elimination of axial bromine and axial hydrogen

Question 18

Which of the following alkynes would give 2-pentanone upon acid-catalyzed hydration?

Accepted Answer

3-pentyne

Question 19

Which of the following is the expected product when 1-bromocyclohexane is treated with $$\mathrm{CH_3OH}$$?

Accepted Answer

1-methoxycyclohexane

Organic Chemistry Reaction Mechanisms, Stereochemistry, and Alkynes: Study Guide

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