Question 1

Which of the following carbocations is the least stable?

Accepted Answer

A methyl carbocation, $$\mathrm{CH_3$^+}$$

Question 2

Which of the following is the strongest acid?

Accepted Answer

Trifluoroacetic acid, $$\mathrm{CF_3COOH}$$

Question 3

Which of the following anions is the strongest base?

Accepted Answer

Methoxide, $$\mathrm{CH_3O^-}$$

Question 4

Which intermediate is formed during the Fischer esterification of acetic acid with ethanol?

Accepted Answer

A tetrahedral intermediate with both an ethoxy and a hydroxy group on the same carbon

Question 5

Which of the following is the correct order of decreasing stability for the conformations of butane (anti, gauche, eclipsed, fully eclipsed)?

Accepted Answer

Anti \u003e Gauche \u003e Eclipsed \u003e Fully Eclipsed

Question 6

Which of the following is an intermediate in the reduction of acetone with sodium hydride ($$\mathrm{NaH}$$)?

Accepted Answer

An alkoxide ion, $$\mathrm{(CH_3$)_2COH^-}$$

Question 7

Which of the following statements about multistep reactions is incorrect?

Accepted Answer

The overall reaction rate is determined by the rate of the fastest step.

Question 8

Why is trifluoroacetic acid ($$\mathrm{CF_3COOH}) a $$stronger acid than acetic acid ($$\mathrm{CH_3COOH}$$)?

Accepted Answer

Because the conjugate base is more stabilized by the electron-withdrawing CF$$_3$$ group.

Question 9

Which of the following is the correct IUPAC name for a molecule with a chlorine atom on carbon 7 and a tert-butyl group on carbon 2 of an octane chain?

Accepted Answer

2-tert-butyl-7-chlorooctane

Question 10

Which of the following is the intermediate in the trans-hydrogenation of 3-hexyne with $$\mathrm{Na/NH_3$(liquid)}$$?

Accepted Answer

A trans-alkenyl radical anion

Question 11

Which of the following is the product of the acid-catalyzed ring-opening of an epoxide with methanol?

Accepted Answer

A trans-1-methoxy-2-hydroxyalkane

Question 12

Which of the following is the most stable carbanion?

Accepted Answer

A benzylic carbanion, $$\mathrm{C_6H_5CH_2^-}$$

Question 13

Which of the following best explains why bromination of alkenes is a stereoselective process?

Accepted Answer

Because the nucleophilic attack occurs only from the side opposite to the bromine atom in the bromonium ion.

Question 14

Which of the following is the correct order of decreasing acidity for the following species: $$\mathrm{CH_3COOH}$$, $$\mathrm{CF_3COOH}$$, $$\mathrm{C_6H_5COOH}$$, $$\mathrm{CH_3CH_2COOH}$$?

Accepted Answer

$$\mathrm{CF_3COOH} \u003e \mathrm{C_6H_5COOH} \u003e \mathrm{CH_3COOH} \u003e \mathrm{CH_3CH_2COOH}$$

Question 15

Which of the following is the major product of acid-catalyzed dehydration of 2-butanol?

Accepted Answer

2-butene, $$\mathrm{CH_3CH=$$CHCH_3$$}$$

Question 16

Which of the following is the correct hybridization for a methyl carbocation, methyl radical, and methyl carbanion, respectively?

Accepted Answer

$$sp^2$$, $$sp^2$$, $$sp^3$$

Question 17

Which of the following is the product of the reaction: $$\mathrm{CH_3CH_2CH_2Br}$$ with $$\mathrm{Mg} in $$dry ether, followed by $$\mathrm{CO_2$}$$ and then acid work-up?

Accepted Answer

Butanoic acid, $$\mathrm{CH_3CH_2CH_2COOH}$$

Question 18

Which of the following is the product of the reaction: 1-butene with $$\mathrm{BH_3$}$$ followed by $$\mathrm{H_2O_2/NaOH}$$?

Accepted Answer

1-butanol, $$\mathrm{CH_3CH_2CH_2CH_2OH}$$

Question 19

Which of the following is the product of the reaction: cyclohexene with $$\mathrm{Br_2$} in $$water?

Accepted Answer

trans-1,2-bromocyclohexanol

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