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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:

  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.

Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.

Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Suggest how you would convert trans-4-methylcyclohexanol to

(a) trans-1-chloro-4-methylcyclohexane.

(b) cis-1-chloro-4-methylcyclohexane.

Q. 15 Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

  1. methyl salicylate
  2. methyl formate (bp 32oC )
  3. ethyl phenylacetate
See all solutions

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