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Identify the indicated sets of protons as unrelated, homotopic, enantiotopic, or diastereotopic:

a.

(b)

(c)

(d)

(e)

(f)

Short Answer

Expert verified
  1. Homotopic
  2. Enantiotopic
  3. Homotopic
  4. Diastereotopic
  5. Homotopic
  6. homotopic

Step by step solution

01

Types of protons

Homotopic means identical.If replacing two protons with a different group (X) gives the same compound then protons are homotopic.

If by replacing two protons with two different groups if the pair shows an enantiomeric relationship then protons are enantiotopic.

If replacing two protons with different groups gives a pair of diastereomers then the protons are diastereotopic.

02

Chart for identification of proton

Initial compound

Chiral center generated after replacement

Types of proton

1

Achiral

No chiral center generated

homotopic

2

Achiral

One chiral center generated

enantiotopic

3

Achiral

More than one chiral center generated

diastereotopic

4

chiral

No chiral center generated

Homotopic

5

Chiral

One or more than one chiral center generated

diastereotopic

03

Proton identification

(a)

The above protons are homotopic. Because after replacement no chiral center is generated.

(b)

The above protons are enantiotopic. Because after replacement one chiral center is generated.

(c)

The protons of -CH3shows a homotopic relationship. As after there is no chiral center generated after their replacement.

(d)

As in the above compound, one chiral center is present and after replacement also a chiral center is generated then the protons show a diastereotopic relationship.

(e)

The protons of -CH3shows a homotopic relationship. As after there is no chiral center generated after their replacement.

(f)

An initial molecule is achiral and after replacement, no chiral center is generated hence the protons show a homotopic relationship.

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Most popular questions from this chapter

Long-range coupling between protons more than two carbon atoms apart is sometimes observed when p bonds intervene. An example is found in 1-methoxy-1-buten-3-yne. Not only does the acetylenic proton, , couple with the vinylic proton , it also couples with the vinylic proton , four carbon atoms away. The data are:

Construct tree diagrams that account for the observed splitting patterns of ,, and .

Compound F, a hydrocarbon with M+= 96 in its mass spectrum, undergoes reaction with HBr to yield compound G. Propose structures for F and G, 13Cwhose NMR spectral data are given below.

a. Compound F Broadband-decoupled 13CNMR: 27.6, 29.3, 32.2, 132.4 d DEPT-90: 132.4 d DEPT-135: positive peak at 132.4 d; negative peaks at 27.6, 29.3, 32.2 d

b. Compound G Broadband-decoupled 13C NMR: 25.1, 27.7, 39.9, 56.0 d DEPT-90: 56.0 d DEPT-135: positive peak at 56.0 d; negative peaks at 25.1, 27.7, 39.9 d

How many absorptions would you expect to observe in the NMR

spectra of the following compounds?

(a) 1,1-Dimethylcyclohexane

(b) CH3CH2OCH3

(c) tert-Butylcyclohexane

(d) 3-Methyl-1-pentyne

(e) cis-1,2-Dimethylcyclohexane

(f) Cyclohexanone

How many 13C NMR absorptions would you expect for cis-1,3-dimethylcyclohexane?For trans-1,3-dimethylcyclohexane? Explain.

How many kinds of electronically non-equivalent protons are present in each of the following compounds, and thus how many NMR absorptions might you expect in each?

aCH3CH2Br(b)CH3OCH2CH(CH3)2(c)CH3CH2CH2NO2(d)Methylbenzene(e)2-Methyl-1-butene(f)cis-3-Hexene

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