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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

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

(a)

(b)

(c)

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

  1. Hexan-2-amine
  2. 2-methylpiperidine
  3. N-ethylpiperidine

5.

6.

Question:An unknown compound gives a molecular ion of m/z 70 in the mass spectrum. It reacts with semicarbazide hydrochloride to give a crystalline derivative, but it gives a negative Tollens test. The NMR and IR spectra follow. Propose a structure for this compound, and give peak assignments to account for the absorptions in the spectra. Explain why the signal at 1790 cm-1 in the IR spectrum appears at an unusual frequency.

(a) Propose a mechanism for the following reaction:

(b) Use the bond-dissociation enthalpies given in Table 4-2 (page 203) to calculate the value of ∆H° for each step shown in your mechanism. (The BDE for is about 280 kJ/mol, or 67 kcal/mol.) Calculate the overall value of ∆H° for the reaction. Are these values consistent with a rapid free-radical chain reaction?
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