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Chapter 12: 13P (page 354)

Question: What alkyl halides would you use to prepare the following ketones by an acetoacetic ester synthesis?

Short Answer

Expert verified

The alkyl halides which you need to use to prepare ketone (a) is 1-bromo-2-methylpropane.

The product of this reaction is

Hence, the-CH2COCH3comes from acetoacetic ester.

The remaining part CH32CHCH2 comes from alkyl halide (1-bromo-2-methylpropane).

Now the mechanism of this reaction is

Step by step solution

01

Subpart (a)

The alkyl halides which you need to use to prepare ketone (a) is 1-bromo-2-methylpropane.

The product of this reaction is

Hence, the-CH2COCH3comes from acetoacetic ester.

The remaining part CH32CHCH2 comes from alkyl halide (1-bromo-2-methylpropane).

Now the mechanism of this reaction is

02

Conclusion

The alkyl halide which you need to use to prepare the given ketone (a) by acetoacetic ester is 1-bromo-2-methylpropane.

03

Subpart (b)

The alkyl halides which you need to use to prepare ketone (b) is 1-bromo-2-phenylethane.

The product of this reaction is

Hence, the 鈥揅H2COCH3 comes from acetoacetic ester.

The remaining part C6H5CH2CH2- comes from alkyl halide (1-bromo-2-phenylethane).

Now the mechanism of this reaction is

04

Conclusion

The alkyl halide which you need to use to prepare the given ketone (b) by acetoacetic ester is 1-bromo-2-phenylethane.

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Most popular questions from this chapter

Phenol,C6H5OH, is a stronger acid than methanol, CH3OH, even though both contain an OH bond. Draw the structures of the anions resulting from loss of H+from phenol and methanol, and use resonance structures to explain the difference in acidity.

Question: By knowing the natural abundances of minor isotopes, it鈥檚 possible to

calculate the relative heights of and M+1 peaks. If 13C has a natural

abundance of 1.10%, what are the relative heights of the and

M+1 peaks in the mass spectrum of benzene, C6H6?

Name the following alkynes, and predict the products of their reaction

With:

(1) H2in the presence of a Lindlar鈥檚 catalyst

(2) H3O+in the presence of H2SO4

Rank the double bonds below in terms of increasing stability:

Question: How could you use infrared spectroscopy to distinguish between the

following pairs of isomers?

(a)HC鈮�CCH2NH2andCH3CH2C鈮�N

(b)CH3COCH3andCH3CH2CHO
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