ma-Q 1) NaH 2) H₂O -XX OH (c) (d) H₂N NO₂ HS. H NO₂ hint: consider that NO₂ can stabilize an adjacent anion on carbon via a resonance effect

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter8: Alkenes: Reactions And Synthesis
Section8.SE: Something Extra
Problem 59AP
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Can you please help with part d. Thank you!

Practice problems:
Propose reasonable mechanisms for the following reactions. Use arrows correctly to indicate bond making and bond
breaking (i.e., movement of electrons), show all mechanistic intermediates, and indicate any formal charges on atoms.
me=&=X=8
(a)
HO
(c)
(d)
H₂N
H* (cat.)
OH (- H₂O)
(b)
HS
0-0
OH
1) NaH
2) H₂O
-N
H
CO₂H
Br Br
NaHCO3
heat
H
a ∞
NO₂
NO₂
hint: consider that NO₂ can stabilize an adjacent anion on carbon via a resonance effect
Br
Transcribed Image Text:Practice problems: Propose reasonable mechanisms for the following reactions. Use arrows correctly to indicate bond making and bond breaking (i.e., movement of electrons), show all mechanistic intermediates, and indicate any formal charges on atoms. me=&=X=8 (a) HO (c) (d) H₂N H* (cat.) OH (- H₂O) (b) HS 0-0 OH 1) NaH 2) H₂O -N H CO₂H Br Br NaHCO3 heat H a ∞ NO₂ NO₂ hint: consider that NO₂ can stabilize an adjacent anion on carbon via a resonance effect Br
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