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Chapter 13: Q.23P (page 682)

Question: Give the spectral assignments for the protons in isobutyl alcohol (Solved Problem 13-4). For example, Ha is a singlet, area = 1, at δ2.4

Short Answer

Expert verified

Answer

From the given diagram, we get to know that,

Ha is a singlet, area 1 atδ 2.4

Hb is a doublet, area 2 atδ 3.4

Hc is a nonuplet, area 1 at δ1.8

Hd is a doublet, area 6 at δ0.9

Step by step solution

01

Isobutyl alcohol

The structure of isobutyl alcohol can be drawn as shown below.

02

Explanation

The spectral assignments for the protons in isobutyl alcohol is shown below.

Chemically different hydrogens

From the diagram, we get to know that,

Ha is a singlet, area 1 at δ2.4

Hb is a doublet, area 2 at δ3.4

Hc is a nonuplet, area 1 at δ1.8

Hd is a doublet, area 6 atδ 0.9

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Most popular questions from this chapter

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 at1.1), yet the product alcohol, a racemic mixture, shows two differentdoublets, one at0.75 and one around1.0.

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

Question: An unknown compound has the molecular formula C9H11Br. Its proton NMR spectrum shows the following absorptions: singlet, d7.1, integral 44 mm singlet, d2.3, integral 130 mm singlet, d2.2, integral 67 mm Propose a structure for this compound.

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.

When 2-chloro-2-methylbutane is treated with a variety of strong bases, the products always seem to contain two isomers (A and B) of formula. When sodium hydroxide is used as base, isomer A predominates. When potassium tert-butoxide is used as the base, isomer B predominates. TheandNMR spectra of A and B are given below.

  1. Determine the structures of isomers A and B.
  2. Explain why A is the major product when using sodium hydroxide as the base and why B is the major product when using potassium tert-butoxide as the base.

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
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