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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 three isomers of dichlorobenzene are commonly named ortho-chlorobenzene, meta-chlorobenzene, and para-chlorobenzene. These three isomers are difficult to distinguish using proton NMR, but they are instantly identifiable using 13C NMR

(a)Describe how carbon NMR distinguishes these three isomers.
(b)Explain why they are difficult to distinguish using proton NMR.

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 at未8.0 andtriplet at未4.0
  2. Sharpsinglet at未2.0 andquartet at未4.1
  3. Sharpsinglet at未3.7 andquartet at未2.3
  4. Broadsinglet at未11.5 andtriplet at未2.3

An inexperienced graduate student was making some 4-hydroxybutanoic acid. He obtained an excellent yield of a different compound, whose 13CNMR spectrum is shown here.

  1. Propose a structure for this product.
  2. Assign the peaks in the 13CNMR spectrum to the carbon atoms in the structure.

Hexamethylbenzene undergoes radical bromination with N-bromosuccinimide to give one monobrominated productand four dibrominated products. These products are easily separated by GC-MS, but the dibrominated products are difficult to distinguish by their mass spectra. Draw the monobrominated product and the four dibrominated products and explain howNMR would easily distinguish among these compounds.

Question:Using a 60-MHz spectrometer, a chemist observes the following absorption: doublet, J = 7 Hz, at 4.00

(a) What would the chemical shift () be in the 500-MHz spectrum?

(b) What would the splitting value J be in the 500-MHz spectrum?

(c) How many hertz from the TMS peak is this absorption in the 60-MHz spectrum? In the 500-MHz spectrum?
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