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Chapter 13: Q3P (page 658)

Determine the number of different kinds of protons in each compounds

  1. 1-bromopropane (b) 2-bromopropane
  2. 2,2-dimethylpropane (d) 2,2-dimethylpentane
  3. (e) 1-chloro-4-methylbenzene (f) 1-chloro-2-methylbenzene

Short Answer

Expert verified

In 1-bromopropane the three types of different hydrogens are present in proton NMR spectra.

They are marked as a, b, and c. So they will provide different proton NMR values.

(a)

Step by step solution

01

1-bromopropane

In 1-bromopropane the three types of different hydrogens are present in proton NMR spectra.

They are marked as a, b, and c. So they will provide different proton NMR values.

(a)

02

2-bromopropane

In 2-bromopropane the two types of different hydrogens are present in proton NMR spectra.

They are marked as a, and b. So they will provide different proton NMR values.

(b)

03

2,2-dimethylpropane

In 2,2-dimethylpropane the one type of hydrogen is present in proton NMR spectra.

They are marked as a. So they will provide same proton NMR value.

(c)

04

2,2-dimethylpentane

In 2,2-dimethylpentane the four types of different hydrogens are present in proton NMR spectra.

They are marked as a, b, c and d. So they will provide different proton NMR values.

(d)

05

1-chloro-4-methylbenzene.

In 1-chloro-4-methylbenzene the three types of different hydrogens are present in proton NMR spectra.

They are marked as a, b, and c. So they will provide different proton NMR values.

(e)

06

1-chloro-2-methylbenzene

In 1-chloro-2-methylbenzene the four types of different hydrogens are present in proton NMR spectra.

They are marked as a, b, c and d. So they will provide different proton NMR values.

(f)

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Most popular questions from this chapter

The following proton NMR spectrum is of a compound of molecular formula C3H80.

  1. Propose a structure for this compound.
  2. Assign peaks to show which protons give rise to which signals in the spectrum.

A bottle of allyl bromide was found to contain a large amount of an impurity. A careful distillation separated the impurity, which has the molecular formula C3H60. The following 13CNMR spectrum of the impurity was obtained:

  1. Propose a structure for this impurity.
  2. Assign the peaks in the13CNMR spectrum to the carbon atoms in the structure.
  3. Suggest how this impurity arose in the allyl bromide sample.

A compound(C10H1202)whose spectrum is shown here was isolated from a reaction mixture containing 2-phenylethanol and acetic acid.

  1. Propose a structure for this compound.
  2. Assign peaks to show which protons give rise to which signals in the spectrum.

A small pilot was adding bromine across the double bond of but-2-ene to make 2,3-dibromobutane. A controller malfunction allowed the reaction temperature to rise beyond safe limits. A careful distillation of the product showed that several impurities had formed, including the one having the NMR spectra that appear below. Determine its structure and assign the peaks to the protons in your structure.

Show how you would distinguish among the following threecompounds

(a)Using infrared spectroscopy and no other information.
(b)Using proton NMR spectroscopy and no other information.
(c)Using 13C-NMR, including DEPT, and no other information.
See all solutions

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