Academic Integrity: tutoring, explanations, and feedback — we don’t complete graded work or submit on a student’s behalf.

1) For each spectral data set, determine the general type (C,CH,CH 2 , or CH 3 )

ID: 897658 • Letter: 1

Question

1) For each spectral data set, determine the general type (C,CH,CH2, or CH3) of each carbon signal. Are there any signals representing more than one carbon? How many degrees of unsaturation are there in each formula?

a. C8H16O2 b. C6H10O3 c. C7H16O d. C7H8

14.0 q 54.1 q 14.4 q 50.2 d

14.3 q 107.1 d 16.6 q 75.3 t

17.1 q 131.2 d 20.1 t 143.3 d

20.4 t 35.5 t

36.0 t 35.6 d

39.4 d 68.3 t

60 t

176.6 s

2) For each spectral data set above, determine the general types of carbons (carbonyl, C=C, or alkyl) for each 13C NMR signal.

3) For each spectral data set above, determine the number of identical carbons generating each signal.

Explanation / Answer

NOTE: 3 questions are asked here we answer first two.

Solution:

(a)

a. C8H16O2 b. C6H10O3 c. C7H16O d. C7H8

14.0 q CH3 54.1 q CH3 14.4 q CH3 50.2 d CH

14.3 q CH3 107.1 d CH 16.6 q CH3 75.3 t   CH2

17.1 q CH3 131.2 d CH 20.1 t CH2   143.3 d   CH

20.4 t CH2 35.5 t   CH2

36.0 t CH2   35.6 d   CH

39.4 d CH 68.3 t   CH2

60 t CH2

176.6 s Carboxylic

Hint: Signal will be split to quartet triplet and doublet by 3 , 2 and 1 proton respectivelly.

(b)

a. C8H16O2 b. C6H10O3 c. C7H16O d. C7H8

14.0 q Alkyl 54.1 q Alkyl   14.4 q Alkyl   50.2 d Alkyl

14.3 q Alkyl   107.1 d C=C   16.6 q Alkyl   75.3 t Alkyl

17.1 q Alkyl   131.2 d C=C 20.1 t Alkyl   143.3 d C=C

20.4 t Alkyl   35.5 t Alkyl

36.0 t Alkyl   35.6 d Alkyl

39.4 d Alkyl   68.3 t Alkyl

60 t Alkyl

176.6 s Carboxylic