Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 22.7, Problem 11P
Draw a resonance structure of the acetonitrile anion, -: CH2C≡N, and account for the acidity of nitriles.
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(a) Compound Z is a tertiary aromatic amine with the formula, C8H11N. Provide a chemical structure for compound Z.
(b)nDraw the structure of the product formed exclusively when nitrous acid reacts with Z.
a) If the pH value of an aqueous solution of trimethylamine [(CH3) 3N] is 10.75, what should be the molarity of this solution? (CH3) 3N + H2O ↔ (CH3) 3NH + + OH-, Kb = 6.3 × 10-5
b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3 + Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7.4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .
The normal pH range for blood plasma is 7.35–7.45. Under these conditions, would you expect the carboxyl group of lactic acid (pKa 3.08) to exist primarily as a carboxyl group or as a carboxylic anion? Explain.
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
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- In each of the following reactions, two possible organic products can be formed. Draw both organic products in each case and then circle the one formed in greatest quantity in each case. HC (a) 1) NaH, 2) acid (b) CH,CH,OH (c) CH,CH,OH NH2 (d) Oarrow_forwarda) If the pH value of an aqueous solution of trimethylamine [(CH3)3N] is 10.75, what should be the molarity of this solution? (CH3)3N + H2O ↔ (CH3)3NH+ + OH-, Kb = 6,3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3+Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7,4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwardDraw the structures of the following compounds:(a) Ethanoic acid(b) Bromopentane(c) Butanonearrow_forward
- How many P – O – P bonds are there in cyclotrimetaphosphoric acid?arrow_forward(a) Give chemical tests to distinguish between(i) Propanal and Propanone, (ii) Benzaldehyde and Acetophenone.(b) How would you obtain(i) But-2-enal from Ethanal, (ii) Butanoic acid from Butanol,(iii) Benzoic acid from Ethylbenzene?arrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forward
- Arrange the following compounds in increasing order of their property as indicated :(i) CH3COCH3, C6H5COCH3, CH3CHO(reactivity towards nucleophilic addition reaction)(ii) Cl—CH2—COOH, F—CH2—COOH, CH3—COOH (acidic character)arrow_forwardGive the chemical tests to distinguish between the following pairs of compounds :(i) Ethyl amine and Aniline(ii) Aniline and Benzylaminearrow_forwardTreating choline with acetic anhydride gives acetylcholine, a neurotransmitter. Write an equation for the formation of acetylcholine. (CH,),NCH,CH,OH Cholinearrow_forward
- (4) Write the structure of the following compounds from their IUPAC names. (a) ethanamide (b) methylethanoate (c) propanoic acid (d) 2-butanone (5) Write the structure of the following ethers and amines from their common names (a) methyl propyl (b) trimethylamine (6) Decide whether the following alcohols are polar or nonpolar (a) CH3CH2CH2CH2CH2CH2CH2OH (b) CH3CH2OHarrow_forwardGive the structural formulae and name the functional groups of the following compounds. (a) 3-chlorobut-1-ene Name the functional group: (b) butanedioic acid Name the functional group: (c) propanamide Name the functional group: (d) 3-methylbutanal Name the functional group:arrow_forwardIdentify which of the statements is/are correct. (i) The molecular formula of the smallest aldehyde is C3H6O, and that of the smallest ketone is also C3H6O. (j) The molecular formula of the smallest carboxylic acid is C2H4O2.arrow_forward
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