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Chapter 20: Q70P (page 1038)

Show a complete mechanism for this reaction.

Short Answer

Expert verified

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the carbonyl oxygen takes place at first.

(b) The lone pair on nitrogen attacks the carbonyl carbon and as a result of it, a cyclopentane ring is created.

(c) A chloride anion from HCI attacks the hydrogen present on the nitrogen.

(d) Protonation of the hydroxy (OH-) group takes place

(e) Removal of water (H2O) molecule.

(f) Addition of methanol (CH3OH)

(g) Lastly, water(H2O) molecule is added again to get the desired product.

Step by step solution

01

Mechanism

All steps involved in the mechanism for the synthesis of the given product is shown as below.

(a) Protonation of the carbonyl oxygen takes place at first.

(b) The lone pair on nitrogen attacks the carbonyl carbon and as a result of it, a cyclopentane ring is created.

(c) A chloride anion from HCI attacks the hydrogen present on the nitrogen.

(d) Protonation of the hydroxy (OH-) group takes place

(e) Removal of water (H2O) molecule.

(f) Addition of methanol (CH3OH)

(g) Lastly, water(H2O) molecule is added again to get the desired product.

02

Mechanistic pathway

The complete mechanism for the reaction

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Most popular questions from this chapter

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

Q.13Most 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.

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

(a)

(b)

(c)

Explain why the acid-catalyzed condensation is a poor method for the synthesis of an unsymmetrical ether such as ethyl methyl ether, CH3CH2 - O - CH3.

For each compound,

  1. Classify the nitrogen containing functional groups.
  2. Provide acceptable name

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)
See all solutions

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