1. An unknown compound is isolated. Mass spectrometry shows M and M+2 peaks at 7

Question

1. An unknown compound is isolated. Mass spectrometry shows M and M+2 peaks at 75.5 and 77.5, at relative abundances of 3:1. IR showed a strong peak at 2261 cm-1 as well as at 931 and 740 cm-1. The following IR and NMR data is given below.

Signal

Shift

Integration

Splitting

A

4.113

2 H’s

singlet

Signal

Shift

Integration

A

24.97

1 C

B

115.06

1 C

a. Determine the molecular formula for the unknown compound

b. How many degrees of unsaturation does the molecule possess

c. List the functional groups that are present in the molecule

d. Identify the structure of the compound

Signal

Shift

Integration

Splitting

A

4.113

2 H’s

singlet

Signal

Shift

Integration

A

24.97

1 C

B

115.06

1 C

Explanation / Answer

a) ClCH2(CN)

b) 2 degree of unsaturation (CN triple bond)

c) Nitrile and alkyl halide

d) Cl-CH2-CN

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