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Midterm

CHM247H1 Midterm: THA Solutions for Subs_Elim_175

3 pages71 viewsSummer 2017

Department
Chemistry
Course Code
CHM247H1
Professor
Cecilia Kutas
Study Guide
Midterm

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THA Solutions S&E page 1 of 3
HA Solutions for Substitution & Elimination Review
THA 1: Which of the substrates at right
would react fastest in an SN2 reaction?
1o substrate with best leaving group
THA 2: Which of the substrates at
right would react fastest in an SN1
reaction?
All LGs the same, so most stable
carbocation rules; this is resonance
stabilized by 2 rings
THA 3: Draw detailed mechanisms for the SN1-type reactions at right.
What is the driving force for the rearrangement (hydride/methide shift) in each
reaction? [Hint: review McM 7.11]
Hydride shift occurs to give the more stable tertiary carbocation.
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