第九章 羧酸及其衍生物
9.1 用系统命名法命名(如有俗名请注出)或写出结构式
a.(CH3)2CHCOOHb.COOHOHc.CH3CH=CHCOOHd.CH3CHCH2COOHBre.CH3CH2CH2COCli.CONH2f.j.(CH3CH2CH2CO)2OHOOCC=CCOOHHHg.CH3 CH2COOC2H5k.邻苯二甲酸二甲酯t.乙酰基h.l.CH3CH2CH2OCOCH3甲酸异丙酯m.N-甲基丙酰胺n---r.略s.苯甲酰基
答案:a. 2-甲基丙酸 2-Methylpropanoic acid (异丁酸 Isobutanoic acid )
b. 邻羟基苯甲酸(水杨酸)o-Hydroxybenzoic acid c. 2-丁烯酸 2-Butenoic acid d 3-溴丁酸 3-Bromobutanoic acid e. 丁酰氯 Butanoyl Chloride f. 丁酸酐 Butanoic anhydride g. 丙酸乙酯 Ethyl propanoate h. 乙酸丙酯 Propyl acetate i. 苯甲酰胺 Benzamide j. 顺丁烯二酸 Maleic acid
COOCH3k.COOCH3Os.Ct.H3COCl.HCOOCH(CH3)2m.CH3CH2CONHCH3
9.2 将下列化合物按酸性增强的顺序排列:
a. CH3CH2CHBrCO2H b. CH3CHBrCH2CO2H c. CH3CH2CH2CO2H d. CH3CH2CH2CH2OH e. C6H5OH f. H2CO3 g. Br3CCO2H h. H2O 答案:
酸性排序 g > a > b > c > f > e > h > d 9.3 写出下列反应的主要产物
a.Na2Cr2O7--H2SO4b.c.(CH3)2CHOH+H3CCOClHOCH2CH2COOHNCCH2CH2CN+H2OLiAlH4NaOHH+d.e.CH2COOHCH2COOHBa(OH)2无水AlCl3CH3f.CH3COCl+g.(CH3CO)2O+OHh.CH3CH2COOC2H5NaOC2H5
i.j.k.CH3COOC2H5CH3CH(COOH)2COOH+CH3CH2CH2OHH++HCl
HOCH2CH2OHLiAlH4H+l.m.2COOH+COOHn.HCOOH+OHNaOC2H5H+o.CH2CH2COOC2H5CH2CH2COOC2H5p.Nq.CONH2OH-+H2NCONH2CH2(COOC2H5)2
COOHCOOHCOOH+COOHH3CCOOCH(CH3)2答案:
a.Na2Cr2O7--H2SO4b.c.(CH3)2CHOH+H3CCOClHOCH2CH2COOHNCCH2CH2CN+H2OLiAlH4NaOHHOCH2CH2CH2OH-d.e.OOCCH2CH2COO-H+HOOCCH2CH2COOHCH2COOHOCH2COOHBa(OH)2无水AlCl3CH3CH3COCH3+COCH3CH3f.CH3COCl+g.(CH3CO)2O+OHOCOCH3h.CH3CH2COOC2H5NaOC2H5CH3CH2COCHCOOC2H5CH3i.j.k.CH3COOC2H5CH3CH(COOH)2COOH+CH3CH2CH2OHH+
+C2H5OHCH3COOCH2CH2CH3+ CO2COOHCH3CH2COOHCl+HCl
l.m.2COOH+HOCH2CH2OHLiAlH4H+COOCH2CH2OOCCOOHn.HCOOH+OHNaOC2H5CH2OHHCOOOCOOC2H5COO-H+o.CH2CH2COOC2H5CH2CH2COOC2H5p.Nq.CONH2OH-+NH2NCONH2+NH3OHNONHOCH2(COOC2H5)2
COOCH3OHOHOH9.4 用简单化学方法鉴别下列各组化合物:
COOHa.COOH与CH2COOHCOOHCH2COOHb.OCH3COOHc.(CH3)2CHCH=CHCOOH与与COOHd.CH3与与COCH3OHCH=CH2
答案:
a. KmnO4 b. FeCl3 c. Br2 or KmnO4 d. ①FeCl3 ②2,4-二硝基苯肼或I2 / NaOH
9.5 完成下列转化:
COOHa.OOHCH3CH2CH2COOH(CH3)2CCOOHOHOOOOOe.(CH3)2C=CH2Ob.c.CH3CH2CH2Br(CH3)2CHOHCH3d.CH3(CH3)3CCOOH
f.BrCOOH
CH3COOC2H5
g.HCCHh.OOCH3CH2COOHCH3COOHOOOCO2CH3OHCH2COONH4CH2CONH2COOHOOCCH3CH3CH2COOCH3CH2CH2CH2COOHCH2(COOC2H5)2i.j.k.l.m.n.CH3CH2COOHCH3CH(COOC2H5)2CH3CH2COOH
COOHOH答案:
a.OHCNCNOHCN-H+H2OH+b.c.CH3CH2CH2BrCH3CH2CH2CN(CH3)2COCOOHCOOHH2OHCNCH3CH2CH2COOH(CH3)2CCNOHOOOOOO(CH3)3CCOOH2)H+ / H2OCOOHBr1)CO2(CH3)2CCOOHOHH2OH+(CH3)2CHOHCH3CrO3.(Py)2d.CH3KMnO4COOHCOOHBa(OH)2e.(CH3)2C=CH2HBr(CH3)3CBrMgEt2O(CH3)3CMgBrf.CH3BrAlCl3H2OH,Hg2++CH3KMnO4COOHBr2FeCH3CH2OHH+g.HCCHCH3CHOKMnO4CH3COOHCH3COOC2H5
h.OHNO3LiAlH4HOOC(CH2)4COOHCH3CH2CH2OHKMnO4HBrOCH3CH2CH2BrMgEt2OCH3CH2CH2MgBri.CH3CH2COOHO+H或CH3CH2CH2CH2CH2OHCH3CH2CH2CH2COOH浓OH-CH3COCH2COOC2H5Cl2P1)EtONa2)CH3CH2CH2BrCN-CH3COCHCOOC2H5CH2CH2CH3CH2COOHCNH3O+CH3(CH2)3COOHj.CH3COOHCH2COOHClCH2(COOC2H5)2CH2COONH4CH2CONH2EtOHk.OOOl.CO2CH3OHm.n.CH3CH2COOHH,NH3+H+H2OSOCl2COOHOH(CH3CO)2OCOOHOOCCH3OHCH3CH2COOCH3CH2COClCH3CH2COOHCH3CH(COOC2H5)2-1)OH2)H+3)
9.6 怎样将己醇、己酸和对甲苯酚的混合物分离得到各种纯的组分? 答案:
己醇ANaHCO3水溶液有机相已醇对甲苯酚NaOH水相已酸钠HCl已酸B水相酚钠HCl酚C已酸B对甲苯酚C有机相已醇A
9.7 写出分子式为C5H6O4的不饱和二元羧酸的各种异构体。如有几何异构,以Z,E标明,
并指出哪个容易形成酐。 答案:
COOHCOOHCOOHCOOHCOOHCOOHHOOCCOOHHOOCHCOOHHOOCCH3COOHCH2
(Z)易成酐 (E) 不易 (Z) 易成酐 (E) 不易成酐
9.8 化合物A,分子式为C4H6O4,加热后得到分子式为C4H4O3的B,将A与过量甲醇及少量硫酸一起加热得分子式为C6H10O4的C。B与过量甲醇作用也得到C。A与LiAlH4作用后得分子式为C4H10O2的D。写出A,B,C,D的结构式以及它们相互转化的反应式。 答案: