Chapter 20: Q.31P (page 1074)
Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Short Answer
Answer
The order of increasing boiling point is,

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Chapter 20: Q.31P (page 1074)
Question: Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

Answer
The order of increasing boiling point is,

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Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline.
Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

5.

6.

The IR, NMR, and mass spectra are provided for an organic compound.


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 Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.
(a) methyl salicylate
(b) methyl formate (bp 32C)
(c) ethyl phenylacetate
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