Circle the number that corresponds to the correct answer for each of the followi

Question

Circle the number that corresponds to the correct answer for each of the following five (5) questions. A. Which reagent reacts with carboxylic acids to form the corresponding methyl esters? 1. diazomethane 2. methyllithium 3. both B. Which of the following compounds is the most acidic? 1. H_3CCHFCO_2H 2. H_3CCHClCO_2H 3. (H_3C)2CHCO_2H C. Which spectroscopic technique can be used to distinguish between heptanal and heptan-2-one? 1. infrared 2. 1^H NMR 3. both D. Which of the following compounds reacts most readily with nucleophiles? 1. heptan-2-one 2. heptanal 3. heptan-2-ol E. Acidic hydrolysis of the following imine affords 1. a ketone 2. an aldehyde 3. a carboxylic acid

Explanation / Answer

1.(A): Carboxylic acid forms methyl ester with diazomethane, however it forms either ketone or anhydride with methylithium. Hence option (1) is correct.

(B): CH3CHFCOOH is the most acidic because the F- is the most electronegative making the carboxylic hydrogen more acidic. Hence option (1) is correct.

(C): We need to use both infrared and 1H NMR spectra to distinguish the two compounds. Hence option (3) is correct.

(D): Higher the partial positive charge on the carbonyl carbon higher is the reactivity of the compound towards a nucleophile. Among the given compounds, the carbonyl carbon in heptanal has the highest partial positive charge as it is attached to a single electron donating alkyl grpoup. Hence option (2) is correct.

(E): Acidic hydrolysis of immine forms ketone and amine. Hence option (1) is correct.

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