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Chapter 20: Q16P (page 674)

How would you prepare 1-phenyl-2-butanone, C6H5CH2COCH2CH3, from benzyl

bromide, C6H5CH鈧侭r? More than one step is required?

Short Answer

Expert verified

Thepreparation of 1-phenyl-2-butanone, C6H5CH2COCH2CH3, from benzyl bromide,

C6H5CH鈧侭r can be explained.

Step by step solution

01

Formation of bonds

The metal Mg reacts with the benzyl bromide for the formation of benzyl magnesium

bromide. There is a breaking of C-Br bond and formation of C-Mg and Mg-Br bonds.

02

1-phenyl-2-butanone formation

The reaction of propanol with benzylmagnesium bromide which follows the acidification

for the formation of 1-phenylbutan-2-ol. The double bond with C and O of propanol c-

can be converted to the single bond of C-O and O-H and also the formation of O-H and

C-C bonds. The oxidation of secondary alcohol to ketone.

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Most popular questions from this chapter

Predict the product of the reaction of p-methyl benzoic acid with each of the following

  1. LiAlH4,鈥�then鈥�H3O+
  2. N-Bromosuccinimide in CCl4
  3. CH3MgBr鈥�in鈥�ether,鈥�then鈥�H3O+
  4. KMnO4,鈥�H3O+

The pKa of p-cyclopropylbenzoic acid is 4.45. Is cyclopropylbenzene likely to be more reactive or less reactive than benzene toward electrophilic bromination? Explain.

Propose structures for carboxylic acids that show the following peaks in their 13C NMR spectra. Assume that the kinds of carbons (1掳, 2掳, 3掳, or 4掳) have been assigned by DEPT-NMR.

a)C7H12O2,25.5未(20),25.9未(20),29未(20),43.1未(30),183未(40)b)C8H8O2,21.4未(1o),128.3未(4o),129未(3o),129.7未(3o),143.1未(4o),168.2未(4o)

Predict the product and provide the mechanism for each reaction below.

Assume you have a mixture of naphthalene and benzoic acid that you want to separate. How might you take advantage of the acidity of one component in the mixture to effect a separation?
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