Part A 1. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SÃ2 and SÃ1 reactions. 2. Can it undergo E2 and E1 reactions? Match the words in the left column to the appropriate blanks in the sentences on the right. Make certain each sentence is co Submit can SN1 SN2 secondary tertiary primary E2 hydrogen cannot E1 carbon Previous Answers Request Answer X Incorrect; Try Again; 3 attempts remaining Reset Help 1. The bulky tert-butyl substituent blocks the back side of the carbon bonded to the bromine to nucleophilic attack, making an SN2 reaction difficult. An SN1 reaction cannot occur because it would require the formation of an unstable primary carbocation. 2. It cannot undergo an E2 reaction, because the B-carbon is not bonded to a hydrogen. It cannot undergo an E1 reaction, because that would require the formation of a tertiary carbocation.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 20E
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Part A
1. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions.
2. Can it undergo E2 and E1 reactions?
Match the words in the left column to the appropriate blanks in the sentences on the right. Make certain each sentence is co
Submit
can
SN1
SN2
secondary
tertiary
primary
E2
hydrogen
cannot
E1
carbon
Previous Answers Request Answer
X Incorrect; Try Again; 3 attempts remaining
Reset Help
1. The bulky tert-butyl substituent blocks the
back side of the carbon bonded to the
bromine to nucleophilic attack, making an
SN2 reaction difficult. An SN1 reaction
cannot occur because it would require the
formation of an unstable primary
carbocation.
2. It cannot undergo an E2 reaction,
because the B-carbon is not bonded to a
hydrogen. It cannot undergo an E1
reaction, because that would require the
formation of a tertiary carbocation.
Transcribed Image Text:Part A 1. Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. 2. Can it undergo E2 and E1 reactions? Match the words in the left column to the appropriate blanks in the sentences on the right. Make certain each sentence is co Submit can SN1 SN2 secondary tertiary primary E2 hydrogen cannot E1 carbon Previous Answers Request Answer X Incorrect; Try Again; 3 attempts remaining Reset Help 1. The bulky tert-butyl substituent blocks the back side of the carbon bonded to the bromine to nucleophilic attack, making an SN2 reaction difficult. An SN1 reaction cannot occur because it would require the formation of an unstable primary carbocation. 2. It cannot undergo an E2 reaction, because the B-carbon is not bonded to a hydrogen. It cannot undergo an E1 reaction, because that would require the formation of a tertiary carbocation.
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