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Mobile App Chapter 14: Q58P (page 527)
As we will learn in Chapter 20, reaction of \({\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)_{\bf{2}}}{\bf{CO}}\) with \({\bf{LiC}} \equiv {\bf{CH}}\) followed by \({{\bf{H}}_{\bf{2}}}{\bf{O}}\) affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 \({\bf{c}}{{\bf{m}}^{{\bf{ - 1}}}}\). D shows the following 1 H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?
Short Answer
Expert verified
Step by step solution
01
Reaction of the carbonyl compound
The nucleophile attacks the carbonyl carbon (acetone). This is because the CO group has the electrophilic position and forms an alcohol, followed by a workup.
02
Step 2: \(^{\bf{1}}{\bf{H}}\) NMR of alcoholic proton
\(^{\rm{1}}{\rm{H}}\) NMR gives a singlet and the broad signal of alcohol proton (OH).
03
Explanation
IR absorption at 3600-3200\({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\): OH,3303\({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\):\({{\rm{C}}_{{\rm{s}}{{\rm{p}}^{\rm{3}}}}}{\rm{ - H}}\)2938\({\rm{c}}{{\rm{m}}^{{\rm{ - 1}}}}\):\({{\rm{C}}_{{\rm{s}}{{\rm{p}}^{\rm{3}}}}}{\rm{ - H}}\)
NMR data: 1.53 (singlet, 6 H, 2 \({\rm{C}}{{\rm{H}}_{\rm{3}}}\)), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm
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