(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy- 4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product. H₂C CI. I, AICI3 Me -OMe 1-methoxy-4-methylbenzene

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
Chapter6: Reactions Of Alkenes
Section: Chapter Questions
Problem 6.38P: Reaction of -pinene with borane followed by treatment of the resulting trialkylborane with alkaline...
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(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy-
4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product.
i
H3C1 CI, AICI 3
Me-
-OMe
1-methoxy-4-methylbenzene
(b) Use phenol as the substrate, propose a synthetic scheme to produce 2-allyl-4-bromophenol (Mechanism not required).
Br
OH
OH
phenol
2-allyl-4-bromophenol
(c) Propose a synthesis of Compound A starting from benzaldehyde and other necessary reagents of your choice (Mechanism not required).
OH
CHO
CI.
Compound A
benzaldehyde
(d) For the given 13C NMR chemical shifts of the carbonyl carbons in the order of ketones > aldehydes > carboxylic acids, provide an explanation.
O
CH3
H3C.
13C NMR Chemical Shifts: H₂C1
H₂C H >
OH
200 ppm
181 ppm
209 ppm
Transcribed Image Text:(a) For the reaction of 1-methoxy-4-methylbenzene with CH3C(O)CI in the presence of AICI3, describe the bonding and electron distribution in 1-methoxy- 4-methylbenzene, formation and structure of the electrophile in the reaction, and the most stable intermediate responsible for the end product. i H3C1 CI, AICI 3 Me- -OMe 1-methoxy-4-methylbenzene (b) Use phenol as the substrate, propose a synthetic scheme to produce 2-allyl-4-bromophenol (Mechanism not required). Br OH OH phenol 2-allyl-4-bromophenol (c) Propose a synthesis of Compound A starting from benzaldehyde and other necessary reagents of your choice (Mechanism not required). OH CHO CI. Compound A benzaldehyde (d) For the given 13C NMR chemical shifts of the carbonyl carbons in the order of ketones > aldehydes > carboxylic acids, provide an explanation. O CH3 H3C. 13C NMR Chemical Shifts: H₂C1 H₂C H > OH 200 ppm 181 ppm 209 ppm
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