Compound e has the formula c 14 h 18 o 3 and is

COMPOUND E has the formula C
14
H
18
O
3
and is related to antioxidants and flavour
compounds found in many plants including corn, peanuts and cocoa beans. Use the IR and NMR
data below to determine the structure of E and enter it on the yellow answer. [14 pts]
HMQC:

Chem 213 Final Examination 2014 CRN10488 Page 15 of 17
Compound F is used as a fragrance and flavour chemical and has the formula C
10
H
16
Compound F does not have any particularly diagnostic IR bands.
38. How many double bond equivalents does Compound F contain?
.
(j) 9
Use the
1
H,
13
C and selected long range HMQC data below to determine the structure of
Compound F and enter it on the yellow sheet [14 pts].
1
H NMR:
13
C{
1
H}
NMR
showing
DEPT-135
phasing:

Chem 213 Final Examination 2014 CRN10488 Page 16 of 17
COMPOUND G has the formula C
10
H
11
NO
2
. Make sure you use your knowledge of chemical
shifts, as well as the IR and NMR data given below, to help you solve this problem. Enter your
structure for G on the yellow sheets. [12 pts]
39. How many double bond equivalents does Compound G contain?
(j) 9
IR: 3480, 3390, 1767 cm
-1
.
40. What functional group is present in Compound G?
(a) C-conjugated ester (b) ketone (c) carboxylic acid
(d) secondary amine (e) O-conjugated ester (f) primary amide
(g) aldehyde (h) alkyne (i) alcohol
Note: the resonance at 4.60 ppm disappears when D
2
O is added.
1
H NMR
(300 MHz):
13
C{
1
H} NMR (DEPT-135 phasing shown in brackets): δ 169.0 (x), 144.1 (x), 140.7 (x),
135.7 (x), 123.7 (x), 119.4 (+), 112.2 (+), 31.0 (-), 25.0 (-), 12.1 (+)
Selected long range (J= 10 Hz) HMQC: δ 4.6 (s) with 123.7 (x), 112.2 (+)
δ 2.95 (t) with 135.7 (x)
δ 2.80 (t) with 169.0 (x), 140.7 (x), 123.7 (x)
δ 2.1 (s) with 144.1 (x), 135.7 (x)

Chem 213 Final Examination 2014 CRN10488 Page 17 of 17
BONUS QUESTION: I recommend you do this last! [15 bonus pts]
COMPOUND H has the formula C
11
H
14
O and is NOT aromatic . Use the
1
H,
13
C and 2D NMR
data to determine the structure of H and enter this on the yellow sheets.
IR: 1053, 902 cm
-1
1
H NMR
(300 MHz):
13
C{
1
H}
DEPT-135
phasing
shown
Long range (J = 10 Hz) HMQC: δ 4.79 (d) and 4.71 (d) with 129.0 (x) and 40.3 (-)
δ 3.67 (t) with 129.0 (x) and 72.1 (-)
δ 2.95 (s) with 129.0 (x) and 116.0 (-)
δ 2.40 (t) with 145.0 (x) and 129.0 (x)
-END-