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Chapter 14: Q.21558-14-58P (page 565)

Question: As we will learn in Chapter 20, reaction of (CH3)2CO withLiC≡CH followed by 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 2120cm-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

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Answer

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:  NMR of alcoholic proton

1H NMR gives a singlet and the broad signal of alcohol proton (OH).

03

Explanation

IR absorption at 3600-3200cm-1 : OH, 3303cm-1 : Csp3-H 2938cm-1 Csp3-H NMR data: 1.53 (singlet, 6 H, 2 CH3), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm

Structure

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Most popular questions from this chapter

Question: Cyclohex-2-enone has two protons on its carbon-carbon double bond (labeled Ha and Hb ) and two protons on the carbon adjacent to the double bond (labeled Hc ). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C=O, its absorption occurs up-field from the signal due to Hb(6.0 vs. 7.0 ppm). Offer an explanation.

Draw all constitutional isomers of molecular formula C3H6Cl2.

a. How many signals does each isomer exhibit in its 1HNMR spectrum?

b.How many lines does each isomer exhibit in its 13CNMR spectrum?

c. When only the number of signals in both 1Hand 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

a. How many signals does dimethyl fumarate (\({\bf{C}}{{\bf{H}}_{\bf{3}}}{{\bf{O}}_{\bf{2}}}{\bf{CCH = CHC}}{{\bf{O}}_{\bf{2}}}{\bf{C}}{{\bf{H}}_{\bf{3}}}\) with a trans C=C) exhibit in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

b. Draw the structure of an isomer of dimethyl fumarate that has each of the following number of signals in its \(^{{\bf{13}}}{\bf{C}}\) NMR spectrum:\(\left( {\bf{1}} \right)\) three; \(\left( {\bf{2}} \right)\) four; \(\left( {\bf{5}} \right)\) five

Identify products A and B from the given 1HNMR data.

a. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1HNMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2H) ppm. What is the structure of A?

b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1HNMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?

How many \(^{{\bf{13}}}{\bf{C}}\) NMR signals do each compound exhibit?

a.

b.

c.

d.

e.

f.

g.

h.
See all solutions

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