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Chapter 8: Q15P (page 418)

Sketch the expected proton NMR spectra of 3,3- dimethylbutanal.

Short Answer

Expert verified

The compound 3,3-dimethylbutanal has a functional group aldehyde.

The structure of 3,3-dimethylbutanal is as shown below:

Step by step solution

01

The structure of 3,3-dimethylbutanal

The compound 3,3-dimethylbutanal has a functional group aldehyde.

The structure of 3,3-dimethylbutanal is as shown below:

02

The proton NMR spectrum of 3,3-dimethylbutanal

The given compound 3,3-dimethylbutanal has the following chemical shift values for chemically different protons.

It has three sets of chemically different protons.

The graph of NMR spectrum is shown below:

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Most popular questions from this chapter

Unknown X, C5 H9 Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5 H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5 H8 O2. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.

The chiral BINAP ligand shown in figure 8-8 contains no asymmetric carbon atoms. Explain how this ligand is chiral.

The structures of three monomers are shown. In each case, show the structure of the polymer that would result from polymerization of the monomer. Vinyl chloride is polymerized to ‘’vinyl’’ plastics and PVC pipe. Tetrafluoroethylene polymerizes to Teflon, used as non-stick coatings and PTFE valves and gaskets. Acrylonitrile is polymerized to Orlon, used in sweaters and carpets.

Vinyl chloride tetrafluoroethylene acrylonitrile

Show how you would accomplish the following synthetic conversions.

(a)But-1-ene -> butan-1-ol

(b)But-1-ene ->butan-2-ol

(c)2-bromo-2,4-dimethylpentane ->2,4-dimethylpentan-3-ol
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