Chapter_4

Organic Chemistry

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-04 JWDD052-Solomons-v2 May 23, 2007 14:26 4 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES SOLUTIONS TO PROBLEMS 4.1 CH 3 (CH 2 ) 5 CH 3 Heptane or CH 3 CH 2 CH(CH 3 )CH 2 CH 2 CH 3 3-Methylhexane or (CH 3 ) 2 CHCH 2 CH 2 CH 2 CH 3 2-Methylhexane or (CH 3 ) 3 CCH 2 CH 2 CH 3 2,2-Dimethylpentane or (CH 3 CH 2 ) 2 C(CH 3 ) 2 3,3-Dimethylpentane or (CH 3 CH 2 ) 3 CH 3-Ethylpentane or (CH 3 ) 2 CHCH 2 CH(CH 3 ) 2 2,4-Dimethylpentane or (CH 3 ) 2 CHCH(CH 3 )CH 2 CH 3 2,3-Dimethylpentane or (CH 3 ) 3 CCH(CH 3 ) 2 2,2,3-Trimethylbutane or 44
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-04 JWDD052-Solomons-v2 May 23, 2007 14:26 NOMENCLATUREANDCONFORMATIONSOFALKANESANDCYCLOALKANES 45 4.2 2-Methylhexane 3-Methylheptane 4-Ethyl-2-methylhexane 2,2,4,4-Tetramethylpentane 2,3,5-Trimethyl-4-propylheptane 2,3-Dimethylbutane 2,3,4-Trimethylpentane 3-Ethyl-3-methylhexane 2,3,5-Trimethylhexane 4.3 (a) Pentyl 1-Methylbutyl 1-Ethylpropyl 3-Methylbutyl 2-Methylbutyl 1,2-Dimethylpropyl 1,1-Dimethylpropyl (b) See the answer to Review Problem 4.1 for the names of C 7 H 16 isomers. 4.4 1-Chlorobutane Cl (a) 1-Chloro-2-methylpropane Cl 2-Chlorobutane Cl 2-Chloro-2-methylpropane Cl
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-04 JWDD052-Solomons-v2 May 23, 2007 14:26 46 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 2-Bromopentane Br (b) 1-Bromopentane Br 2-Bromo-3-methylbutane Br 3-Bromopentane 1-Bromo-2,2-dimethylpropane 2-Bromo-2-methylbutane Br Br 1-Bromo-3-methylbutane Br 1-Bromo-2-methylbutane Br Br 4.5 (b) OH 1-Pentanol 2-Pentanol OH OH 3-Pentanol OH 3-Methyl-2-butanol OH 2,2-Dimethyl-1-propanol 2-Methyl-2-butanol OH (a) 1-Butanol 2-Butanol OH OH 2-Methyl-1-propanol OH OH 2-Methyl-2-propanol 3-Methyl-1-butanol OH OH 2-Methyl-1-butanol
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-04 JWDD052-Solomons-v2 May 23, 2007 14:26 NOMENCLATUREANDCONFORMATIONSOFALKANESANDCYCLOALKANES 47 4.6 (a) 1,1-Dimethylethylcyclopentane or tert -butylcyclopentane (b) 1-Methyl-2-(2-methylpropyl)cyclohexane or 1-isobutyl-2-methylcyclohexane (c) Butylcyclohexane (d) 1-Chloro-2,4-dimethylcyclohexane (e) 2-Chlorocyclopentanol (f) 3-(1,1-Dimethylethyl)cyclohexanol or 3- tert -butylcyclohexanol 4.7 (a) 2-Chlorobicyclo[1.1.0]butane (b) Bicyclo[3.2.1]octane (c) Bicyclo[2.1.1]hexane (d) 9-Chlorobicyclo[3.3.1]nonane (e) 2-Methylbicyclo[2.2.2]octane (f) Bicyclo[3.1.0]hexane or bicyclo[2.1.1]hexane 4.8 (a) trans -3-Heptene (b) 2,5-Dimethyl-2-octene (c) 4-Ethyl-2-methyl-l-hexene (d) 3,5-Dimethylcyclohexene (e) 4-Methyl-4-penten-2-ol (f) 2-Chloro-3-methylcyclohex-3-en-1-ol 4.9 (b) (e) (h) (a) (d) (g) (j) (c) (f) (i) Cl Br Br Br Cl Cl Cl Cl
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-04 JWDD052-Solomons-v2 May 23, 2007 14:26 48 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 4.10 1-Hexyne 2-Hexyne 3,3-Dimethyl- 1-butyne 3-Methyl-1-pentyne 4-Methyl-1-pentyne 4-Methyl-2-pentyne 3-Hexyne 4.11 0 ° 60 ° 120 ° 180 ° 240 ° 300 ° 360 ° H 3 C H 3 C H H CH 3 H H 3 C H 3 C H H CH 3 H H 3 C H H CH 3 CH 3 H H 3 C H 3 C H CH 3 H H H 3 C H H H CH 3 H 3 C H 3 C H H H CH 3 CH 3 H 3 C H H H H 3 C CH 3 Rotation
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Chapter_4 - P1: PBU/OVY JWDD052-04 P2: PBU/OVY QC: PBU/OVY...

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