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

Question 2

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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?
 Treatment of 2-hexanone with NaOCH<sub>2</sub>CH<sub>3</sub> followed by CH<sub>3</sub>Br affords compound X (C<sub>7</sub>H<sub>14</sub>O)  as the major product. X shows a strong absorption in the IR spectrum at 1713 cm<sup>?1</sup>, and its <sup>1</sup>H NMR data is given below. What is the structure of X?     \begin{array}{llcc}   \text {Signal \#  } &  \text { Shift (ppm)  }  &  \text {Multiplicity } &  \text {Integration }\\ 1&0.96& \text {triplet}&3 \mathrm{H}\\ 2&1.16& \text {doublet}&3 \mathrm{H}\\ 3&1.33& \text {multiplet}&2 \mathrm{H}\\ 4&1.53&\text {multiplet}&2 \mathrm{H}\\ 5&2.09& \text {singlet}&3 \mathrm{H}\\ 6&2.52& \text {multiplet}&1 \mathrm{H} \end{array}    A)  IV B)  III C)  II D)  I

Signal #  Shift (ppm)  Multiplicity Integration 10.96triplet3H21.16doublet3H31.33multiplet2H41.53multiplet2H52.09singlet3H62.52multiplet1H\begin{array}{llcc} \text {Signal \# } & \text { Shift (ppm) } & \text {Multiplicity } & \text {Integration }\\1&0.96& \text {triplet}&3 \mathrm{H}\\2&1.16& \text {doublet}&3 \mathrm{H}\\3&1.33& \text {multiplet}&2 \mathrm{H}\\4&1.53&\text {multiplet}&2 \mathrm{H}\\5&2.09& \text {singlet}&3 \mathrm{H}\\6&2.52& \text {multiplet}&1 \mathrm{H}\end{array}
 Treatment of 2-hexanone with NaOCH<sub>2</sub>CH<sub>3</sub> followed by CH<sub>3</sub>Br affords compound X (C<sub>7</sub>H<sub>14</sub>O)  as the major product. X shows a strong absorption in the IR spectrum at 1713 cm<sup>?1</sup>, and its <sup>1</sup>H NMR data is given below. What is the structure of X?     \begin{array}{llcc}   \text {Signal \#  } &  \text { Shift (ppm)  }  &  \text {Multiplicity } &  \text {Integration }\\ 1&0.96& \text {triplet}&3 \mathrm{H}\\ 2&1.16& \text {doublet}&3 \mathrm{H}\\ 3&1.33& \text {multiplet}&2 \mathrm{H}\\ 4&1.53&\text {multiplet}&2 \mathrm{H}\\ 5&2.09& \text {singlet}&3 \mathrm{H}\\ 6&2.52& \text {multiplet}&1 \mathrm{H} \end{array}    A)  IV B)  III C)  II D)  I


A) IV
B) III
C) II
D) I

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