PSETorgANS.DOC

Chemistry 101 Mrs. Freschl Organic Problem Set Answers 1. Nomenclature: Draw the structural formula for the following compounds a) isobutyl bromide b) ortho nitrotoluene c) 3,3-diethyl-4-sec.butylnonane d) para isobutylaniline e) carbon tetrachloride CCl4 f) isopropylcyclopentane g) acetylene HC?CH h) 3-hexyne CH3CH2C?CCH2CH3 i) 3,4-dipropylbenzoic acid j) 1,3-cyclopentadiene k) 3-phenyl-1-propene (page 2) l) meta dibromobenzene m) cyclohexyne n) 2-chloro-4-tert.butylphenol o) cis 1,2-dibromocyclopentane p) 2-amino-5-isopropyldecane q) 3-methyl cyclopentene r) trans 2-pentene s) 2,2,4,4-tetramethylheptane t) 1,4-pentadiene u) cyclopentylbenzene v) 3-benzyl-1-hexyne (page 3) II. Give the IUPAC name for the following compounds a) sec. butyl bromide 2-bromobutane b) 2-bromo-4-ethylphenol c) CH3(CH2)5CH3 heptane d) 1,2-dinitrobenzene or ortho dinitrobenzene e) 2-methyl-2-pentene f) 2,4,5-tribromobenzoic acid g) 2,6-dimethyl-4-ethyl-4-tert.butyloctane h) 5-methyl-1,4-heptadiene i) 1-bromo-1-isobutylcyclopentane (page 4) j) trans 5-bromo-5-methyl-2-heptene k) 2-methyl-4-tert.butylaniline l) CH3CH(CH3)CH2CH(CH3)CH2CH3 2,4-dimethylhexane m) cis 1,4-diethylcyclohexane n) 3-phenyl-1-butyne o) 4,4-diethyl-1-heptene p) 2,2,6,6-tetramethyl-3-octyne q) 3,3,7-trimethyl-5-sec.butyldecane r) (CH3)3CCH2CH2CH(CH3)2 2,2,5-trimethylhexane (page 5) s) 4-ethyl-6-tert.butyl-6-isobutyldecane t) 2,5-dimethyl-2,6-octadiene III. Which compounds are aromatic? A, E, F (give all answers) A) B) C) D) E) F) IV. Draw TWO structural isomers for: a) and b) 2-methylphenol or or V. For the following compound: Draw two structural isomers or or cyclobutane Draw one geometric isomer (page 6) VI. Isomers What is the relationship between the following pairs of compounds? Use the answers: (SI) structural isomers, (GI) geometric isomers (SM) same molecule (N) no relationship a) & (SM) b) CH2=CHCH2CH3 & CH3CH=CHCH3 (SI) c) & (N) d) & (SI) (8 carbons) (7 carbons) (2-ethylphenol) (3-ethylphenol) e) & (SI) f) CH2=CHCH=CH2 & HC?CCH2CH3 (SI) (2-pentene) (1-pentene) (C4H6) (C4H6) g) & (SI) h) & (SI) (C5H10) (C5H10) (1,4-dibromo) (1,2-dibromocyclohexane) i) & (SI) j) & (SM) (1,2-dibromo) (1,1-dibromocyclopentane) (trans 1,4-dibromocyclohexane) k) & (SM) l) & (GI) (cis 1,2-dibromocyclohexane) (trans 1,4-dibromo?.) (cis 1,4-dibromo?.) m) & (GI) n) & (SM) (cis 2-pentene) (trans 2-pentene) (2-methylbutane) (page 7) VII. Reactions Give the structure of the major organic product for the following reactions. Put an ?O? after any oxidation reaction, put an ?S? after any substitution and put an ?A? after any addition reaction. S a) CH3CH2CH3 & Br2/heat ? and A b) CH3CH=CH2 & Br2 ? (no cis or trans in alkanes) A c) CH3CH=CH2 & HCl ? O d) CH3CH2CH=CH2 & dilute cold KMnO4 ? (no cis or trans in alkanes) A e) CH3CH2CH=CH2 & H2O/acid catalyst ? A f) & excess H2/catalyst ? A g) CH3C?CH & excess Br2 ? A h) & Br2 ? (Ignore cis versus trans) A i) CH3CH2CH2C?CH & excess H2/catalyst ? O j) CH3CH=CH2 & burning (O2) ? 3CO2 and 3H2O A k) CH3CH2C?CH & excess HCl ? (page 8) A l) 1-butene & H2O/H3O+ ? A m) 1-butyne & excess HBr ? A n) CH3CH2CH=CH2 & Br2 ? (no cis or trans in alkanes) S o) & Cl2/heat ? A p) & H2O/acid catalysis ? A q) & HCl ? A r) CH2=CHCH2CH=CH2 & excess Br2 ? (no cis or trans in alkanes) A s) & H2O/H2SO4 ? A t) & Br2 ? (Ignore cis versus trans) O u) CH3CH=CHCH3 & dilute cold KMnO4 ? (no cis or trans in alkanes) A v) CH2=CHCH2CH=CH2 & excess HBr ?