14. Why is 4-nitrobenzoic acid more acidic than benzoic acid? The nitro group is

Question

14. Why is 4-nitrobenzoic acid more acidic than benzoic acid? The nitro group is electron withdrawing and helps to stabilize the negative charge on the conjugte bse B) 4-nitrobenzoic acid has a higher molecular mass. C) The nitro group makes the aromatic ring unstable. D) The nitro group is electron donating and helps to stabilize the negative charge on the 15. Oxidation of a 1° alcohol with pyridinium chlorochromate results in the production of A) an ester B) a ketone C) an aldehyde D) an ether E) none of the above 16. How would the following compounds be distinguishable using IR and NMR spectroscopy? A) The NMR of compound 1 will have two singlets: B) The C O absorption in the IR spectrum of compound 1 will be at a higher wave number than that of compound 2. C) The NMR of compound 2 will have one triplet at a chemical shift of about 4. The NMR of compound 1 will have two singlets AND the C O absorption in the IR spectrum of - compound 1 will be at a higher wave number than that of compound 2. 17. Why is phenol more acidic than ethanol? A) It has more carbons. B) Steric hindrance C) The negative charge on the phenoxide anion can be stabilized by resonance. D) Ethanol is more acidic. 18. Cyclic esters are called: A) lactones. B) lactams. C) lacrimals. D) imides. E) enamines. 19. Which of the following reaction pathways could be used to convert a carboxylic acid into an acid chloride? A) Heat the acid with hydrochloric acid B) React the acid with thionyl chloride (SOC12) C) React the acid with sodium chloride D) Fuse the acid with sodium chloride 20. Carboxylic acids can be made from Grignards by treating the Grignard reagents with: A) carbon monoxide B) esters C) aldehydes D) diborane E) carbon dioxide

Explanation / Answer

Ans 14 : A) The nitro group is electron withdrawing and helps to stabilise the negative charge on the conjugate base.

Nitro group being the electron withdrawing group drags the electron towards itself. This becomes easier to loose H+ and the conjugate base becomes more stable due to presence of less electrons over it.

This results in 4-nitrobenzoic acid to be more acidic than benzoic acid.

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