Question

Please answer this question step by step. I'm very weak in Org chem. ___ 13. A...

Please answer this question step by step. I'm very weak in Org chem.

___ 13.

A compound has the formula C8H9Br. Its 1H NMR spectrum consists of:

       doublet, d 2.0

       quartet, d 5.15

       multiplet, d 7.35

The IR spectrum shows two peaks in the 680-840 cm-1 region; one is between 690 and 710 cm-1 and the other is between 730 and 770 cm-1. Which is a possible structure for the compound?

A)

p-BrC6H4CH2CH3

D)

C6H5CHBrCH3

B)

p-CH3C6H4CH2Br

E)

3,4-Dimethyl-1-bromobenzene

C)

C6H5CH2CH2Br

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Answer #1

The right answer is C6H5CHBrCH3 (Option D).

Explanation: The phenyl ring protons (5H, C6H5) gives a multiplet at 7.35 ppm.

The proton on the bromine-attached carbon (1H, CHBr) gives a quartet at 5.15 ppm

The methyl protons (3H, CH3) gives a doublet at 2.0 ppm.

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