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Identify the compound that has an M 1 1 ion at mYz 5 136 in its CI mass spectrum, an IR

Chapter 23, Problem 23.4

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QUESTION:

Identify the compound that has an M 1 1 ion at mYz 5 136 in its CI mass spectrum, an IR absorption at 3279 cm1 , and the following NMR spectrum: d 0.91 (1H, s), d 1.07 (3H, t, J 5 7 Hz), d 2.60 (2H, q, J 5 7 Hz), d 3.70 (2H, s), d 7.18 (5H, apparent s).

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QUESTION:

Identify the compound that has an M 1 1 ion at mYz 5 136 in its CI mass spectrum, an IR absorption at 3279 cm1 , and the following NMR spectrum: d 0.91 (1H, s), d 1.07 (3H, t, J 5 7 Hz), d 2.60 (2H, q, J 5 7 Hz), d 3.70 (2H, s), d 7.18 (5H, apparent s).

ANSWER:

Problem 23.4

Identify the compound that has an M 1 1 ion at mYz 5 136 in its CI mass spectrum, an IR absorption at 3279 cm1 , and the following NMR spectrum: d 0.91 (1H, s), d 1.07 (3H, t, J 5 7 Hz), d 2.60 (2H, q, J 5 7 Hz), d 3.70 (2H, s), d 7.18 (5H, apparent s).

                                                                Step by Step Solution

Step 1 of 2

From the given,

Cl mass spectrum the  ion has .

Hence, its mass comes out to be 135.

Therefore, according to the nitrogen rule it has an odd number of nitrogen atoms.

IR absorption at .

This value indicates secondary amine  stretching.

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