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

---

Definitions:

Standard Error

Estimates the variability of sample mean measurements around the population mean, indicating the precision of the sample mean as an estimate of the population mean.

Confidence Interval

Values derived from sample analyses, that fall within a range likely to encompass the parameter of an unseen population.

Sample

A subset of a population selected for measurement, observation, or questioning to provide statistical information about the population.

Standard Error

The standard deviation of the sampling distribution of a statistic, typically the mean, indicating the accuracy of a sample mean estimate relative to the population mean.