Identify products A and B from the given \({}^{\bf{1}}{\bf{H}}\) NMR data.

(A) Treatment of \({\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{ = CHCOC}}{{\bf{H}}_{\bf{3}}}\) with one equivalent of HCl forms compound A. A exhibits the following absorptions in its \({}^{\bf{1}}{\bf{H}}\)NMR 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 \(\left( {{{\left( {{\bf{C}}{{\bf{H}}_{\bf{3}}}} \right)}_{\bf{2}}}{\bf{C = O}}} \right(\)with dilute aqueous base forms B. Compound B exhibits four singlets in its \({}^{\bf{1}}{\bf{H}}\) NMR 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?

Short Answer

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a.

b.

Step by step solution

01

Step 1: \({}^{\bf{1}}{\bf{H}}\) NMR spectrum

The number of signals in\({}^{\bf{1}}{\bf{H}}\)NMR spectrum of a compound depends on the chemical environment of the protons (hydrogen atoms) present in it.

The protons that share the same chemical environment resonate at the same frequency and hence give only a single signal.

02

Identifying the compound A

The reaction of \({\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{ = CHCOC}}{{\rm{H}}_{\rm{3}}}\) HCl is provided below.

Reaction of \({\rm{C}}{{\rm{H}}_{\rm{2}}}{\rm{ = CHCOC}}{{\rm{H}}_{\rm{3}}}\) with HCl

03

Verifying the structure of compound A

The NMR signals given by the hydrogen atoms present in the compound is as follows:

NMR signals are shown by the protons of compound A

The signals are by following per under the spectral data of compound A.

04

Identifying the compound B

The reaction of acetone with a dilute aqueous base is represented below.

Reaction of acetone with a base

05

 \({}^{\bf{1}}{\bf{H}}\) NMR signals shown by compound B

The figure given below represents the hydrogen atoms present in compound B along with their chemical shift and splitting pattern.

NMR signals are shown by the protons of compound B

The NMR shifts shown by the hydrogen atoms of compound B are by following per under the spectral data provided.

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Most popular questions from this chapter

Question: For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.

a.

b.

c.

Draw all constitutional isomers of molecular formula \({{\bf{C}}_{\bf{3}}}{{\bf{H}}_{\bf{6}}}{\bf{C}}{{\bf{l}}_{\bf{2}}}\).

a. How many signals does each isomer exhibit in its \({}^{\bf{1}}{\bf{H}}\) NMR spectrum?

b. How many lines does each isomer exhibit in its \({}^{{\bf{13}}}{\bf{C}}\) NMR spectrum?

c. When only the number of signals in both \({}^{\bf{1}}{\bf{H}}\) and \({}^{{\bf{13}}}{\bf{C}}\) NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?

Question:Propose a structure consistent with each set of spectral data:

a. C4H8Br2: IR peak at 3000–2850cm-1 ;

NMR (ppm):

1.87 (singlet, 6 H)

3.86 (singlet, 2 H)

b. C3H6Br2: IR peak at 3000–2850cm-1 ;

NMR (ppm):

2.4 (quintet)

3.5 (triplet)

c. C5H10O2: IR peak at 1740cm-1 ;

NMR (ppm):

1.15 (triplet, 3 H) 2.30 (quartet, 2 H)

1.25 (triplet, 3 H) 4.72 (quartet, 2 H)

d . C6H14O: IR peak at 3600-3200 cm-1 ;

NMR (ppm):

0.8 (triplet, 6 H) 1.5 (quartet, 4 H)

1.0 (singlet, 3 H) 1.6 (singlet, 1 H)

e. C6H14O: IR peak at 3000-2850cm-1 ;

NMR (ppm):

1.10 (doublet, relative area = 6)

3.60 (septet, relative area = 1)

f . C3H6O: IR peak at 1730cm-1 ;

NMR (ppm):

1.11 (triplet)

2.46 (multiplet)

9.79 (triplet)

Question: Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.

a. CH3CH2CH2CH2OH ; 13CNMR: 14, 19, 35, and 62 ppm

b. (CH3)2CHCHO ; 13C NMR: 16, 41, and 205 ppm

c. CH2=CHCHOHCH3 ; 13C NMR: 23, 69, 113, and 143 ppm

Question: What effect does increasing the operating frequency of a1HNMR spectrum have on each value: (a) the chemical shift inδ ;(b) the frequency of an absorption in Hz; (c) the magnitude of a coupling constant J in Hz?

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