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Chapter 20: Q21P. (page 1067)

Question: Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a)propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b)methyl cyclohexyl ketone from cyclohexanecarboxylic acid

Short Answer

Expert verified

(a)

(b)

Step by step solution

01

Synthesis of ketones

The synthesis of ketones is done by different methods,such as the oxidation of alcohols, alkenes, and alkene cleavage.Other ways to synthesize ketones are the alkylation of an acid and Friedel-Crafts acylation.

02

Formation of propiophenonefrom propionic acid

(a) The first method for the formation of propiophenone from propionic acid is by the alkylation of an acid.



Formation of propiophenonefrom propionic acid

The second method for the formation of propiophenone from propionic acid is by using Friedel-Crafts acylation.

Formation of propiophenonefrom propionic acid

03

Formation of methylcyclohexylketone from cyclohexanecarboxylic acid

(b) The formation of methylcyclohexyl ketone from cyclohexanecarboxylic acid is done as follows:



Formation of methylcyclohexylketone from cyclohexanecarboxylic acid

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Most popular questions from this chapter

(a) How many asymmetric carbon atoms are there in an aldotetrose? Draw all the aldotetrose stereoisomers.

(b) How many asymmetric carbon atoms are there in a ketotetrose? Draw all the ketotetrose stereoisomers.

(c) How many asymmetric carbon atoms and stereoisomers are there for an aldohexose? For a ketohexose?

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents.

(c) Diethyl carbonate is a liquid reagent that is easy to handle. In contrast, phosgene is a highly toxic and corrosive gas. Show how you might use diethyl carbonate instead of phosgene to make Lexan庐. Also, show how you might use diethyl carbonate instead of methyl isocyanate to make Sevin庐 insecticide.

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of 螖贬 for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it鈥檚 there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.
See all solutions

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