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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

Answer the following questions for each compound:

a. How many signals are in its 13C NMR spectrum?

b. Which signal is at the lowest frequency?

Draw a splitting diagram for Hbwere

a.Jba= 12 Hz andJbc= 6Hz b.Jba= 12 Hz andJbc= 12Hz

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

Which has a greater chemical shift for the proton, the proton H1NMR spectrum of pure ethanol or the proton H1NMR spectrum of ethanol dissolved in CH2Cl2.

Propose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.)

a. The1HNMR spectrum of a compound with molecular formulaC4H10O2has two singlets with integral ratios of 2: 3.

b. The1HNMR spectrum of a compound with molecular formulaC6H10O2has two singlets with integral ratios of 2: 3.

c. The1HNMR spectrum of a compound with molecular formulaC8H6O2has two singlets with integral ratios of 1: 2.
See all solutions

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