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Briefly explain why OtBu- sometimes favored over hydroxide as an elimination reagent?

Briefly explain why OtBu- sometimes favored over hydroxide as an elimination reagent?

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Briefly explain why OtBu- sometimes favored over hydroxide as an elimination reagent?

a) Works best with bulky bases: SN1 SN2 E1 E2 b) Requires antiperiplanar geometry: SN1 SN2 E1 Е2 c) The mechanism involves a carbocation intermediate: SN1 SN2 E1 E2 d) The mechanism has two steps: SN1 SN2 E1 E2 e) Rate increases with better leaving groups: SN1 SN2 Е1 E2 f) Stereochemistry in inverted : SN1 SN2 E1 Е2 g) Zaitsev product is formed SN1 SN2 E1 Е2 h) Rate increases with concentration of the substrate: SN1 SN2 Е1 Е2 i) Rate increases in aprotic solventsSN1 SN2 Е1 E2
Transcribed Image Text:a) Works best with bulky bases: SN1 SN2 E1 E2 b) Requires antiperiplanar geometry: SN1 SN2 E1 Е2 c) The mechanism involves a carbocation intermediate: SN1 SN2 E1 E2 d) The mechanism has two steps: SN1 SN2 E1 E2 e) Rate increases with better leaving groups: SN1 SN2 Е1 E2 f) Stereochemistry in inverted : SN1 SN2 E1 Е2 g) Zaitsev product is formed SN1 SN2 E1 Е2 h) Rate increases with concentration of the substrate: SN1 SN2 Е1 Е2 i) Rate increases in aprotic solventsSN1 SN2 Е1 E2
81.1 Label the reaction most likely to take place (E1,SN1, E2, SN2 or a combination of these) under the following conditions. Draw the major product(s), include stereochemistry when relevant. а) f) Br -OtBu CH3CH2OH b) CI g) НОСН Br NaČN, DMF → Br -OCH3 h) Br H20 d) Br "CH3 i) Br e) KOTBU > PCN (CH3)2CO j) CLNOH
Transcribed Image Text:81.1 Label the reaction most likely to take place (E1,SN1, E2, SN2 or a combination of these) under the following conditions. Draw the major product(s), include stereochemistry when relevant. а) f) Br -OtBu CH3CH2OH b) CI g) НОСН Br NaČN, DMF → Br -OCH3 h) Br H20 d) Br "CH3 i) Br e) KOTBU > PCN (CH3)2CO j) CLNOH
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