An alkyl bromide reacts with an alkoxide ion to form a compound whose 1 H NMR sp

Question

An alkyl bromide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown below. Draw the alkyl bromide and the alkoxide ion.

Hint: Read about Williamson ether synthesis.

Note: If your answer contains a metal salt, omit the metal and draw the compound as an anion.

An alkyl bromide reacts with an alkoxide ion to form a compound whose 1H NMR spectrum is shown below. Draw the alkyl bromide and the alkoxide ion. Hint: Read about Williamson ether synthesis. Note: If your answer contains a metal salt, omit the metal and draw the compound as an anion.

Explanation / Answer

NMR:

Two singlets at 1.20ppm and 3.20ppm

Ratio of protons is 3:1 respectively

Assuming that the singlet at 3.20ppm = 3 protons (-CH3 group),
The singlet at 1.20ppm = 9 protons (3 x

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