Ме, Мe Si., НО Ме HO `Me HO H КCN, HCN Ме `CI Me `CN PPTS EtzN MezSio Me Me,SiO Me NH2 OH Me LIAIH4 H2SO4 aq. `CN H3O* benzen Dean-Stark pH = 6

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy
Section14.SE: Something Extra
Problem 42AP
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Indicate the complete mechanisms for each step of the synthesis below.

Ме, Ме
Si,
НО Ме
HO
HO
H.
КCN, HCN
Ме
`CI
Me
"Ме
CN
PPTS
EtzN
MezSiO Me
NH2
OH
Me
Me,SiO Me
LIAIH4
H2SO4 aq.
`CN
H30*
benzen
Dean-Stark
pH = 6
Transcribed Image Text:Ме, Ме Si, НО Ме HO HO H. КCN, HCN Ме `CI Me "Ме CN PPTS EtzN MezSiO Me NH2 OH Me Me,SiO Me LIAIH4 H2SO4 aq. `CN H30* benzen Dean-Stark pH = 6
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