Briefly explain why OtBu- sometimes favored over hydroxide as an elimination reagent? a) Works best with bulky bases:SN1SN2E1E2b) Requires antiperiplanar geometry:SN1SN2E1Е2c) The mechanism involves a carbocation intermediate:SN1SN2E1E2d) The mechanism has two steps: SN1SN2E1E2e) Rate increases with better leaving groups:SN1SN2Е1E2f) Stereochemistry in inverted :SN1SN2E1Е2g) Zaitsev product is formedSN1SN2E1Е2h) Rate increases with concentration of the substrate:SN1SN2Е1Е2i) Rate increases in aprotic solventsSN1SN2Е1E2 81.1 Label the reaction most likely to take place (E1,SN1, E2, SN2 or a combination of these) under thefollowing conditions. Draw the major product(s), include stereochemistry when relevant.а)f)Br-OtBuCH3CH2OHb)CIg)НОСНBrNaČN, DMF →Br-OCH3h)BrH20d)Br"CH3i)Bre)KOTBU >PCN(CH3)2COj)CLNOH

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Answered: Briefly explain why OtBu- sometimes…

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

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 53AP

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Question

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

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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