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Chapter 14: Q70P (page 678)

How canH1NMR be used to prove that the addition of HBr to propene follows the rule that says that the electrophile adds to the sp2 carbon bonded to the most hydrogens?

Short Answer

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Formation of 2-bromopropane

Step by step solution

01

Step-by-Step Solution Step 1: The addition  of HBr  to propene

The addition of HBr to propene is an electrophilic substitution reaction. HBr provides an electrophileH+. This electrophile attacks the double bond to form a primary and secondary carbocation. As secondary carbocation is most stable compared to the primary carbocation, therefore, the major product formed is 2-bromopropane.

02

The signals  in NMR

2-bromopropane gives one doublet and one septet signal in H1NMR spectra. But if the electrophile adds to the sp2carbon bonded to the least number of hydrogens it gives three signals in the H1NMR spectrum.

Formation of 2-bromopropane

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Most popular questions from this chapter

a) For the following compounds which pairs of hydrogen (Ha and Hb) are enantiotopic hydrogens?

b) which pairs are diastereotopic hydrogens?

Identify each of the following compounds from its molecular formula and its IR and 1H NMR spectra:

a.C5H12O

b. C6H12O2

c. C4H7ClO2

d. C4H8O2

Identify each of the following compounds from its molecular formula and its H1NMR spectrum:

a.C8H8

b.C6H12O

c.C9H18O

d.C4H8O

How many signals are produced by each of the following compounds in its

a.1HNMRSpectrum?

b. 13CNMR spectrum?

1.

2.

3.

4.

5.

6.

Draw a diagram like the one shown in Figure 14.12 to predict;

a. the relative intensities of the peaks in a triplet.

b. the relative intensities of the peaks in a quintet.
See all solutions

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