20.2 Outline a procedure for separating a mixture

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(g) (h) NH2 NH 2 N NH Br 2 NHCl NCl PhSO 2Cl no reaction NH 2 Br Br NaOH Br no reaction NSO 2Ph no reaction (i) Tetrapropylammonium chloride dissolves in water to give a neutral solution, however, tetrapropylammonium hydroxide gives a strong basic solution. 20.33 Describe with equations how you might separate a mixture of aniline, p-cresol, benzoic acid, and toluene using ordinary laboratory reagents. Solution: N
mixture H+ separation NH3 OH - mixture OH- separation NH2 H + CH 3 NaHCO 3 separation OH CH 3 COONa 20.34 Show how you might synthesize β-aminopropionic acid (H 3NCH 2CH 2CO 2 - ) from succinic anhydride. (β-Aminopropionic acid is used in the synthesis of pantothenic acid; see Problem 18.34.) Solution: O O O O + NH 3 H 2C C H 2C C O NH 2 Br/OH - OH H 2C NH 2 H 2C C O O H + H + COOH H 3NCH 2CH 2CO 2 20.35 Show how you might synthesize each of the following form the compounds indicated and any other needed reagents. (a) (CH3)3 + N(CH2)10 + N(CH3)32Br - from 1,10-decanediol (b) Succinylcholine bromide (see the chapter opening vignette) from succinic acid, 2-bromoethanol, and trimethylamine Answers: (a) (b) HO(CH 2) 10OH 2HBr Br(CH 2) 10Br 2N(CH 3) 3 H3C N HOOC 2N(CH 3) 3 COOH 2BrCH 2CH 2OH O O CH 3 CH 3 (CH3) 3N(CH2) 2OC(CH2) 2CO(CH2) 2N(CH3) 3 2Br (CH 2) 10N CH 3 CH 3 O O 2Br CH 3 Br(CH 2) 2OC(CH 2) 2CO(CH 2) 2Br
Page 1 and 2: 20.1 Outline a procedure for separa
Page 3 and 4: O H H H 2,Ni N 20.6 Reductive amina
Page 5 and 6: (e) CH 3 NBS/hv CH 2Br NaCN (i) LiA
Page 7 and 8: 20.12 Suggest how you might modify
Page 9 and 10: (d) (e) NHCOCH 3 NHCOCH 3 NHCOCH 3
Page 11 and 12: Br NH 2 NO2 CuBr Br N 2 + (1) Br 2
Page 13 and 14: analgesic) Answer: A: H3CH2CO N N O
Page 15 and 16: 20.21 Write structural formulas of
Page 17 and 18: O HO N O Cl - N + (o) Pyrrolidine (
Page 19 and 20: (g) Phenlacetamide (a) (b) (c) (d)
Page 21 and 22: O O O (c) P-Nitroaniline NH C O (d)
Page 23 and 24: CH 3CH 2CH 2 NH 2 CH 3CH 2CH 2OH (b
Page 25 and 26: (a) N N O (b) 20.30 Give structure
Page 27 and 28: H 3C (q) H3C (r) H3C NC Answer: (a)
Page 29 and 30: Br O 2N Br (l) (m) Br (1)Zn/HCl (2)
Page 31: (c) (d) (e) (f) NH 2 CH 3 NHCH 3 NH
Page 35 and 36: 20.39 Using reactions that we have
Page 37 and 38: H 3C N Answer: H 3C H N CH3 CH3 H 2
Page 39 and 40: ion.) Answer: (a) (b) H N H N CH 3
Page 41: (b) Propose a mechanism for formati

20.2 Outline a procedure for separating a mixture

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