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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

Identify each compound below from its molecular formula and its 13CNMR spectrum.

(a) C11H22O

(b) C8H9Br

(c) C6H10O

(d) C6H12

How can theirH1NMR spectra distinguish the following compounds?

Identify each of the following compounds from the 1H NMR data and molecular formula:

a.C4H8Br2: a 6H singlet at 1.97 ppm

a 2H singlet at 3.89 ppm

b. C8H9Br: a 3H doublet at 2.01 ppm

a 1H quartet at 5.14 ppm

a 5H broad singlet at 7.35 ppm

c. C5H10O2: a 3H triplet at 1.15 ppm

a 3H triplet at 1.25 ppm

a 2H quartet at 2.33 ppm

a 2H quartet at 4.13 ppm

Where would you expect to find the H1NMR signal of (CH3)2Mgrelative to the TMS signal? (Hint: Magnesium is less electronegative than silicon.)

Propose a mechanism for proton exchange of an alcohol in aqueous base.
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