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

Question:In a 300-MHz spectrometer, the protons in bromomethane absorb at a position 660 Hz downfield from TMS.

(a) What is the chemical shift of these protons?

(b) What is the chemical shift of the bromomethane protons in a 60-MHz spectrometer?

(c) How many hertz downfield from TMS would they absorb at 60 MHz?

Each of these four structures has molecular formula . Match the structure with its characteristic proton NMR signals. (Not all of the signals are listed in each case.)

  1. Sharpsinglet atδ8.0 andtriplet atδ4.0
  2. Sharpsinglet atδ2.0 andquartet atδ4.1
  3. Sharpsinglet atδ3.7 andquartet atδ2.3
  4. Broadsinglet atδ11.5 andtriplet atδ2.3

Predict the chemical shifts of the protons in the following compounds

Sets of spectra are given for two compounds. For each set,

(1) Look at each spectrum individually and list the structural characteristics you can determine from that spectrum.

(2) Look ar the set of spectraas a group and purpose a tentative structure.

(3) Verify that your proposed structure accounts for the major features of each spectrum. The solution for compound 1 is given after the problem but go as far as you can before looking at the solution.

Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown. The proton NMR of 2-methylpropanal shows the two methyl groups as equivalent (one doublet at δ 1.1), yet the product alcohol, a racemic mixture, shows two different 3H doublets, one at δ 0.75 and one around δ 1.0

(a)Draw a Newmann projection of the product along the C1-C2 axis.
(b)Explain why the two methyl groups have different NMR chemical shifts. What is the term applied to protons such as these?
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