2 organic chemistry questions, please explain steps (15 pts) The functional grou

Question

2 organic chemistry questions, please explain steps (15 pts) The functional group found in the leftmost structure below is a carboxylic acid. Two thiocarboxylic acid variations are found in the middle (thioic S-acid) and right most (thioic O-acid) structures. Assume the rate of reaction of the carboxylic acid functional group with excess strong nucleophile is 1. Will the thioic S-acid and thiic O-acid be slower or faster than this baseline? Explain your response based on what we have learned about the Ady mechanistic step. .

Explanation / Answer

Question 1.

Obviously, the thioic S-acid and the thioic O-acid will be slower than the baseline (carboxylic acid).

Explanation:

In the case of thioic S-acid, the electronegativity of S(C-S, sp3-hybridized) is less than that of O(C-O, sp3-hybridized), as a result, the thioic S-acid is less electrophilic, hence the thioic S-acid will be slower than the baseline.

In the case of thioic O-acid, the electronegativity of S(C=S, sp2-hybridized) is less than that of O(C=O, sp2-hybridized), as a result, the thioic O-acid is less electrophilic, hence the thioic S-acid will be slower than the baseline.

Question 2.

The reagents for condition B:

Clemmenson reduction: Zinc-amalgam (Zn-Hg), Conc. HCl (Or) Wolf-Kishner reduction: Hydrazine (H2N-NH2), KOH

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