Concept explainers
(a)
Interpretation:
It is to be explained how the
Concept introduction:
The
(b)
Interpretation:
It is to be explained how the meta isomer of nitro phenol has the highest
Concept introduction:
Greater the resonance stabilization of the conjugate base, stronger is the acid. The electron withdrawing group withdraws electron from ortho and para position effectively than from the meta position by resonance effect. Thus, the electron density at ortho and para positions is reduced than that at meta.
Want to see the full answer?
Check out a sample textbook solutionChapter 6 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- The pka of phenol (C6H5OH) is 10.0. When a nitro group (NO2) is attached to the ring, the pK, decreases, as shown for the ortho, meta, and para isomers. OH OH ОН OH NO2 (a) Explain why the pK, values of all three isomers are lower than the pka of phenol itself. (b) Explain why the meta isomer has the highest pka of `NO2 Phenol NO2 the three isomers. pKa = 10.0 7.23 8.35 7.14arrow_forwardPhthalic acid and isophthalic acid have protons on two carboxy groupsthat can be removed with base. (a) Explain why the pKa for loss of thefirst proton (pKa1) is lower for phthalic acid than isophthalic acid. (b)Explain why the pKa for loss of the second proton (pKa2) is higher forphthalic acid than isophthalic acid.arrow_forwardPQ-3. What is the major product of this reaction? (A) CN H (B) CN O CN CN H (D) HCN OH CNarrow_forward
- 3. Which is the stronger acid: (a) Benzoic acid with a Ka of 6.5 x10-5 or hydrocyanic acid with a Ka of 4.9 x 10-10? (b) Boric acid with a pKa of 9.14 or carbonic acid with a pKa of 6.37arrow_forwardThioglycolic acid, HSCH2CO2H, a substance used in depilatory agents (hair removers) has pKa = 3.42. What is the percent dissociation of thioglycolic acid in a buffer solution at pH = 3.0?arrow_forwardEleostearic acid, C18H30O2, is a rare fatty acid found in the tung oil used for finishing furniture. On ozonolysis followed by treatment with zinc, eleostearic acid furnishes one part pentanal, two parts glyoxal (OHC-CHO), and one part 9-oxononanoic acid [OHC(CH2)7CO2H]. What is the structure of eleostearic acid?arrow_forward
- но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.arrow_forward(a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forwardMatch each of the following pk, values (3.2, 4.9, and 0.2) to the appropriate carboxylic acid: (a) CH;CH,COOH; (b) CF3COOH; (c) ICH;COOH.arrow_forward
- Which compound in each pair is more basic: (a) (CH3)2NH and NH3; (b) CH3CH2NH2 and ClCH2CH2NH2?arrow_forwarda) Calculate Ka of formic acid whose pKa= 3.75. b) Calculate pKa of nitromethane whose Ka= 5.0 x 10"arrow_forwardProvide the approximate pK, of the following and indicate the most acidic hydroge (a) CH3-NH-CH3 (b) CH3-C=CH (c) CH3-COOH (d) CH3-CH2-OHarrow_forward