An aldol condensation reaction using the reagents acetone and benzaldehyde, in the presence of sodium hydroxide was used to produce dibenzylacetone. Give a detailed NMR analysis for the product (address the issue of double bond stereochemistry;  3J values are sensitive to double bond geometry see diagram below).

Chemistry for Engineering Students
3rd Edition
ISBN:9781285199023
Author:Lawrence S. Brown, Tom Holme
Publisher:Lawrence S. Brown, Tom Holme
Chapter1: Introduction To Chemistry
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Problem 1.77PAE
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An aldol condensation reaction using the reagents acetone and benzaldehyde, in the presence of sodium hydroxide was used to produce dibenzylacetone. Give a detailed NMR analysis for the product (address the issue of double bond stereochemistry;  3J values are sensitive to double bond geometry see diagram below).

На
Ho
R
Ho
3Jah = 6 to 12 Hz
3J.. = 12 to 18 Hz
2Jpc =0 to 3 Hz
'bc
Transcribed Image Text:На Ho R Ho 3Jah = 6 to 12 Hz 3J.. = 12 to 18 Hz 2Jpc =0 to 3 Hz 'bc
H1-NMR @400 MHz: dibenzalacetone in CDCI3
Sample 13
Curent Daa Paaners
NAME
2010-Thun-Ada
PROCNO
12- Acquition Parameter
Dae
1843
PULROG
SOLVENT
NS
16
FIDRES
1.457779 sec
RO
0 usee
25.61 usec
2973K
1.00000000 sec
DE
TE
TDO
CHANNEL
NUCI
PI
PLI
PLIW
11ue
-250 d
18.35 e W
410 Me
12- Procesing perameten
32760
430.130005 M
"TMS
7.7
7.6
7.5
7.4
7.3
7.2
7.1
Ppn
8.5
8.0
7.5
7.0
6.5
6.0
5.5
5.0
4.5
4.0
3.5
3.0
2.5
2.0
1.5
1.0
0.5 ppm
幽自自
TO'D
BD'L -
Transcribed Image Text:H1-NMR @400 MHz: dibenzalacetone in CDCI3 Sample 13 Curent Daa Paaners NAME 2010-Thun-Ada PROCNO 12- Acquition Parameter Dae 1843 PULROG SOLVENT NS 16 FIDRES 1.457779 sec RO 0 usee 25.61 usec 2973K 1.00000000 sec DE TE TDO CHANNEL NUCI PI PLI PLIW 11ue -250 d 18.35 e W 410 Me 12- Procesing perameten 32760 430.130005 M "TMS 7.7 7.6 7.5 7.4 7.3 7.2 7.1 Ppn 8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 ppm 幽自自 TO'D BD'L -
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