Elimination Reactions of Alkyl Halides; Competition Between Substitution and Elimination Quiz 2

1.

Which of the following is not a true statement? [Hint] Syn elimination is the removal of two substitutents from the same side of the molecule. Anti elimination is favored over syn elimination in an E2 reaction. Syn elimination requires the molecule to be in a staggered conformation. Syn elimination is slower than anti elimination. Anti elimination is the removal of two substitutents from opposite sides of the molecule.

2.

Which of the following describes the stereochemistry of an E2 reaction? [Hint] stereospecific regioselective and stereospecific regioselective stereoselective regioselective and stereoselective

3.

What alkene is formed as the major product of an E2 reaction between 2-bromohexane and hydroxide ion? [Hint] (E)-3-hexene (Z)-2-hexene

(Z)-3-hexene (E)-2-hexene 1-hexene

4.

What product is formed when HBr is eliminated from (2S,3S)-2-bromo-3-phenylbutane in an E2 reaction? [Hint] (Z)-3-methyl-3-phenyl-1-butene (E)-3-methyl-3-phenyl-1-butene (Z)-2-phenyl-2-butene and (E)-2-phenyl-2-butene (Z)-2-phenyl-2-butene (E)-2-phenyl-2-butene

5.

Which of the following statements is not true? [Hint] The product of the E2 reaction of 1-chloro-2,3-dimethylcyclohexane is 1,2dimethylcyclohexene. The product of the E2 reaction of cis-1-chloro-2-methylcyclohexane is 3methylcyclohexene. The product of the E2 reaction of trans-1-chloro-2-methylcyclohexane is 3methylcyclohexene. The product of the E1 reaction of 1-chloro-2,3-dimethylcyclohexane is 1,2dimethylcyclohexene. The product of the E1 reaction of 1-chloro-1,2-dimethylcyclohexane is 1,2dimethylcyclohexene.

6.

Why does cis-1-bromo-4-tert-butylcyclohexane react faster in an E2 reaction than does trans1-bromo-4-tert-butylcyclohexane? [Hint]

When Br and H are in the required equatorial positions, the large tert-butyl group is in the more stable axial position. When Br and H are in the required equatorial positions, the large tert-butyl group is in the more stable equatorial position. The required syn elimination can occur with all the substituents in the most stable equatorial position. Since the Br is in an equatorial position, syn elimination can occur. When Br and H are in the required axial positions, the large tert-butyl group is in the more stable equatorial position.

7.

Which of the following equations defines the "deuterium kinetic isotope effect"? [Hint] kH/kD kD - kH (kH - kD)/kD kD / kH kH - kD

8.

What size of ring is formed from the intramolecular reaction of Br-CH2-(CH2)3-CH2-O-? [Hint] a 3-membered ring a 4-membered ring a 5-membered ring a 6-membered ring a 7-membered ring

9.

Which of the following alkyl halides would form the greatest yield of 3-heptene as a result of reaction with methoxide ion? [Hint] 2-bromoheptane 5-bromoheptane 4-bromoheptane 3-bromoheptane 1-bromoheptane

10 .

What is the most likely reaction for a primary halide to undergo in the presence of relatively small base/nucleophile? [Hint] SN1 E1 E2 E1 and SN1 SN2