DSP

If turning in late, provide explanation here: ______________________________________Accomodation

CHEM 3AL Lab E: Crossed-Aldol Condensation Data Analysis (Unknown Y)
adapted from Dr. Pete Marsden and Dr. Alexis Shusterman
1: What was your product? Based on the NMR spectra included on pages 4 and 5 of
this document, determine the structure of your major product and starting material.

UNKNOWN CODE: Y

ALDEHYDE PRODUCT
g base G
+ -/-*=-
H *, -- ↑
-I
KI
-one
( MeO-- -
2 Ome

Provide at least 4 pieces of evidence (one from each category below) and
reasoning connecting the evidence to your conclusion. If the evidence was
inconclusive, explain.

EVIDENCE EXPLANATION
LIMITING Since ketone is the limiting reagent &
Mdehyce is
REAGENT: in excess , the double favored
rondensation put is .

nuetone
________
130-132 C
°
MELTING The literature mpr is
.

RANGE: Sincer the experimental mpr matches the literature

mpr ,
it's the right product .

130 4 132"
________
.
-

COUPLING Since J 15 4 H2 is within the trans alkene

range
=
.

CONSTANT: 112-18 H2) the put contains 2 trues alkenes

,
.

. 4 Hz
15
________
OTHER NMR C from the One
Since
only unisaldehyde has sp3
EVIDENCE: The
13
group ,
it has a penk -8-88 ppon region.

<NMR has
two
a penk ~55 ppm
other starting uldenyces only
have

________ Sp"C .

Page 1 of 5
 2: Draw a mechanism showing the formation of your major product.

G G
g NUUH
- -
~-x+=-
-H + Haf
mer-KE -Y
I↑
z +
ZH, U
Ky
-one & -
Ome
-H
Of a
-
OUH >
-

-
:Q G
I Woul
·
- >
-

I↓
>
& 1
-

- I --_ -
OMe
Hal
H TH
-
Me He -come
I
-
>
-
GGH
80 g E
Y
I 2
I-
-/-*=-
i je
- to
TI
-

TY T H
-

I -
-come
DELOME
:
- =
MeO-- -
- F
+ x 1
come
-

Ome &
--
(
Me
2
i Hat

=
H8

. It E
-
=KI
↓ Hy
*
↑
-ome
I
med-
>

UH
I
-

↑ - =
&
Me8 -'I x*
>
-

↑-I-
-
Mef -
Ome -
Ome

GOH

MW 58 08 0 U5 mL MW 136 15 0 144 MW 244 34

0 135
. .

y
3: How much did you make? Convert your ACTUAL amounts into ymmol.
.
.
. .

0 741 glmL .

I ketone + 2 aldehyde → I final product

0 .

85x GalyxAmr x
/Ormm _____
8 mmol 1.462 mmol
_____ _____
↓. U46 mmol

Based on the ACTUAL amounts above, calculate your % yield (show work):
↓. U46 mmul
(88
6 75
x

U 681 mmul
.
%
.

4: How pure was it?

EXPLAIN:
Since the crude lune had 2 spots
--

--- --- Sketch one of your TLC .

to
plates. Based on the TLC verysteIlization
was
necessary
data, was recrystallization the It was
purify crude .

necessary? If so, was it bl I spot

successful there's only
successful? How do you
the recrystallized
know? If the data is remaining in

inconclusive, explain that put lune .

So ,
it became more

instead. ⑳
WV-8 pure
Orde
.

⑭
⑳ ⑳

.......
· I- SM Crude Revyst
cryst

ne
e
identitBlur Ritea material
U 125
.
.
0 125 0 08
.
.
.
Page 2 of 5

recryst recrystallized .
6 06
.
U UG
product
.
5: Spectral Analysis
Analyze the 1H and 13C NMR spectra for your unknown product that are provided on
the next two pages. You will need to draw the structure of your product in the indicated
boxes, label the structures with letters, and then label the signals on the spectra with the
corresponding letter(s).

Examples for how to label your structures with letters are provided below. Effectively,
have label “A” as close to the carbonyl as possible, then increase lettering as you move
toward the end of the molecule.

Pay attention to any other specific directions written on the spectra.

Page 3 of 5
1H NMR of product from aldehyde Y in CDCl3

7.73 3 9 .6 6 .6
7.69 3 75.7 69 .3
7.59 3 36. 8.5
7.57 3 7.5 99.
6.98 793.9 96 .
6.95 779.9 3 .9 CHCl3
6.94 778. 79.
6.93 77 . 85.

4.0

6.0
7.60 7.55 7.50 7.45 7.40 7.35 7.30 7.25 7.20 7.15 7.10 7.05 7.00 6.95 6.90
alculate the coupling constant f1 (ppm)
for the highest ppm doublet. E
l according to the instructions on page 3
3891 6-3875
. .
7 * B>A
>D
= 15 4 . H2
+ G
Je L StB ↳ 1 o -B [
-/----
D~- X

E "I
MeO-C
-
A A

L
--p
I
z

-
E
w D & Ome
D
A D +

B hen labeling the signals with letters

C
C
CHCl3 . appro i atel 6.9

ou can una biguousl assign all other signals. Remember to consider resonance.
2.0

4.0

6.0

6.0
7.8 7.6 7.4 7.2 7.0 6.8 6.6 6.4 6.2 6.0 5.8 5.6 5.4 5.2 5.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6
f1 (ppm)
13C[1H] NMR of product from aldehyde Y in CDCl3

Draw and label the product according to the instructions on page 3 peci icall assign the signals at
pp and pp
D l3
he re aining signals should be
assigned in three groups
G
E E L E
1
-1)/---
F- -D e e ber to consider pea heights
-Y
A z F
all ~ I
It B B
I
MeO--E E -
G I * penk heights
& Ome
F
F 1) # of H attached
↓ # ofIt shorter
,

2) & # of C
integral , ,

taller

full : E + F

medium : B L +
H

Short : D G +

190 185 180 175 170 165 160 155 150 145 140 135 130 125 120 115 110 105 100 95 90 85 80 75 70 65 60 55 50 45
f1 (ppm)