raw the appropriate Newman projection which leads to the major E2 ELIMINATION product. int 1: Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, I. OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformation. Red bond = the location of a double bond in the final product and the direction of a Newman projection. int 2: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You have to decide if beta-H or beta-D atom will be eliminated to form the major product. You will have to draw two Newman projections and decide which one is the most stable (energetically). CH₂ -Br CH₂ draw anti-periplanar conformation (leading to major elimination product)

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
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Question 10
Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product.
Hint 1: Review Chapter 10.3. the elimination can only occur if the leaving group (Cl, Br. 1, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformation. Red bond = the location of a double bond in the final product and the direction of a Newman projection.
Hint 2: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You have to decide if beta-H or beta-D atom will be eliminated to form the major product. You will have to draw two Newman projections and decide which one is the most stable (energetically).
CH.
H-D
HBr
CHy
draw anti-periplanar conformation
(leading to major elimination product)
A
B
C
CH₂
H.
Br
H.
Br
Br
Br
`CHy
H.C
CH₂
CHy
major Newman
CH₂
CHy
CH₂
major Newman
major Newman
major Newman
C
OD
Transcribed Image Text:Question 10 Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product. Hint 1: Review Chapter 10.3. the elimination can only occur if the leaving group (Cl, Br. 1, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformation. Red bond = the location of a double bond in the final product and the direction of a Newman projection. Hint 2: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You have to decide if beta-H or beta-D atom will be eliminated to form the major product. You will have to draw two Newman projections and decide which one is the most stable (energetically). CH. H-D HBr CHy draw anti-periplanar conformation (leading to major elimination product) A B C CH₂ H. Br H. Br Br Br `CHy H.C CH₂ CHy major Newman CH₂ CHy CH₂ major Newman major Newman major Newman C OD
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