5. + 6.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...
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5. + 6.

Twelve constitutional isomers exist with the molecular formula C4H¬Br. Answer the following questions
concerning their reactivity in substitution/elimination reactions. Assume no rearrangements occur.
Br
Br
Me
Me
Br
Me
Br
Me
Br
Me
Me
A
В
C
D
E
F
Me
Me
Me
Br
Br
Br
Br
Br
Br
Me
Me
G
J
K
1.
Which 2 isomers would react fastest in an SN2 reaction?
2. Which 4 isomers could participate in both SN1 and E2?
3. Which 4 isomers could create terminal alkenes in bimolecular elimination?
4. Which 2 isomers would not work in E1/E2 but could react in SN1/SN2?
5. Which 4 isomers would not participate in substitution or elimination?
6.
Which isomer could participate in SN1 but not SN2?
7. Which 3 isomers contain secondary leaving groups?
8.
Which 3 isomers could create resonance stabilized carbocations?
1
Transcribed Image Text:Twelve constitutional isomers exist with the molecular formula C4H¬Br. Answer the following questions concerning their reactivity in substitution/elimination reactions. Assume no rearrangements occur. Br Br Me Me Br Me Br Me Br Me Me A В C D E F Me Me Me Br Br Br Br Br Br Me Me G J K 1. Which 2 isomers would react fastest in an SN2 reaction? 2. Which 4 isomers could participate in both SN1 and E2? 3. Which 4 isomers could create terminal alkenes in bimolecular elimination? 4. Which 2 isomers would not work in E1/E2 but could react in SN1/SN2? 5. Which 4 isomers would not participate in substitution or elimination? 6. Which isomer could participate in SN1 but not SN2? 7. Which 3 isomers contain secondary leaving groups? 8. Which 3 isomers could create resonance stabilized carbocations? 1
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