You react an unknown aldehyde (substitutent group marked with an "x") with a ketone and get the product on the right (substitutent group still unknown). HNMR data for the product is shown below. Which of these 3 aldehydes is the reactant that was used?

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
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You react an unknown aldehyde (substitutent group marked with an "x") with a ketone and get the product on the right (substitutent group still unknown).

HNMR data for the product is shown below. Which of these 3 aldehydes is the reactant that was used?

sorry the HNMR looks rough, this was the last question on my final and I am still kinda reeling from it.

Unknown Aldehyde
y
Possibilities
0
H
H
to or
H
H
OCH₂
9-8ppm
+
j
M my
5-6ish Rom
кам
3
t
Product
2-3ish ppm
0
CH₂
#
Rough
NMR
Product
Transcribed Image Text:Unknown Aldehyde y Possibilities 0 H H to or H H OCH₂ 9-8ppm + j M my 5-6ish Rom кам 3 t Product 2-3ish ppm 0 CH₂ # Rough NMR Product
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