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Chapter 15: Q64P (page 733)

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

Short Answer

Expert verified

Reaction followed as:

Step by step solution

01

Formation of butan-2-one

The formation of butan-2-one from the butane is a multistep process.

Firstly, bromination is done followed by the reaction with the acetic acid in then on hydrolysis the alcohol formation takes place which leads to ketone on reduction.

02

Mechanism

Mechanism followed as:

  1. Bromination occurs that the addition of bromide ion in presence of hv

  2. Alkyl bromide reacts with carboxylic acid

  3. Hydrolysis

  4. Alcohol formation occurs

  5. React with Na2Cr2O7 followed by sulphuric acid

  6. Ketone formation occurred

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Most popular questions from this chapter

Problem:D. N. Kursanov, a Russian chemist, proved that the bond that is broken in the hydroxide-ion-promoted hydrolysis of an ester is the acyl C-O bond, rather than the alkyl C-O bond, by studying the hydrolysis

of the following ester under basic conditions:

a. What products contained the label?

b. What product would have contained the label if the alkyl C-O bond had broken?

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.

Propose a mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride

a.Identify the two products obtained from the following reaction:

b. A student carried out the preceding reaction, but stopped it before it was half over, whereupon he isolated the major product. He was surprised to find

that the product he isolated was neither of the products obtained when the reaction was allowed to go to completion. What product did he isolate?

Rank the following amides from greatest reactivity to least reactivity toward acid-catalyzed hydrolysis:
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