Treatment of 2-Hexanone with NaOCH₂CH₃ Followed by CH₃Br Affords Compound

question 38

Multiple Choice

Treatment of 2-hexanone with NaOCH₂CH₃ followed by CH₃Br affords compound X (C₇H₁₄O) as the major product. X shows a strong absorption in the IR spectrum at 1713 cm^-1, and its ¹H NMR data is given below. What is the structure of X?
$\begin{array}{|l|l|l|l|}\hline \text { Signal } & \text { Shift } & \text { Multiplicity } & \text { Integration } \\& (\mathbf{p p m}) & \\\hline 1 & 0.96 & \text { triplet } & 3 \mathrm{H} \\\hline 2 & 1.16 & \text { doublet } & 3 \mathrm{H} \\\hline 3 & 1.33 & \text { multiplet } & 2 \mathrm{H} \\\hline 4 & 1.53 & \text { multiplet } & 2 \mathrm{H} \\\hline 5 & 2.09 & \text { singlet } & 3 \mathrm{H} \\\hline 6 & 2.52 & \text { multiplet } & 1 \mathrm{H} \\\hline\end{array}$

• A) I
• B) II
• C) III
• D) IV

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