4_all_ - 4.1 Write condensed structural formulas for all of...

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4.1 Write condensed structural formulas for all of the constitutional isomers with the molecular formula C 7 H 16 (There is a total of nine constitutional isomers). Answer: Heptane 2-methylhexane 3-methylhexane 2,2-dimethylpentane 2,3-dimethylpentane 2,4-dimethylpentane 2,2,3-trimethylbutane 3,3-dimethylpentane 3-ethylpentane 4.2 (a) In addition to the 2,2-dimethylpropyl (or neopentyl) group just given, there are seven other five-carbon groups. Write their structures and give each structure its systematic name. (b) Provide IUPAC names for the nine C7H16 isomers that you gave as answers to problem 4.1. Answer: H 3 C H 2 C C H 2 H 2 C C H 2 H 3 C CH C H 2 H 2 C CH 3 H 3 C H 2 C CH H 2 C CH 3 H 3 C H 2 C C H 2 CH CH 3 H 3 C CH CH CH 3 CH 3 H 3 C H 2 C C CH 3 CH 3 H 3 C C H 2 CH H 2 C CH 3 Pentyl 3'-methylbutyl 2'-methylbutyl 1'-methylbutyl 1',2'-dimethylpropyl 1',1'-dimethylpropyl 1'-ethylpropyl
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4.3 Give IUPAC substitutive names for all of the isomers of (a) C 4 H 9 Cl and (b) C 5 H 11 Br Answer: (a) Cl Cl Cl Cl 1-Chlorobutane 2-Chlorobutane 1-Chloro-2-methylpropane 2-Chloro-2-methylpropane (b) Br Br Br Br Br Br Br Br 1-Bromopentane 2-Bromopentane 3-Bromopentane 1-Bromo-3-methylbutane 1-Bromo-2-methylbutane 2-Bromo-2-methylbutane 2-Bromo-3-methylbutane 1-Bromo-2,2-dimethylpropane 4.4 Give IUPAC substitutive name for all of the isomeric alcohols with the formulas (a) C 4 H 10 O and (b) C 5 H 12 O. Answer: (a) CH 3 CH 2 CH 2 CH 2 OH 1-Butanol H 3 C H 2 C CH OH 3 2-Butanol H 3 CC H H 2 C 3 OH 2-methyl-1-propanol H 3 OH 3 3 2-methyl-2-propanol
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(b) CH 3 CH 2 CH 2 CH 2 CH 2 OH 1-pentanol H 3 C H 2 C H 2 C H C CH 3 OH 2- pentanol H 3 C H 2 C H C H 2 C CH 3 OH 3- pentanol H 3 C H 2 C C H H 2 C OH CH 3 2-methyl-1-butanol H 3 C H 2 C C 3 3 OH 2-methyl-2-butanol H 3 C H C C H 3 3 OH 3-methyl-2-butanol H 2 C H 2 C C H 3 3 OH 3-methyl-1-butanol H 3 CC 3 3 2 OH 2,2-dimethyl-1-propanol 4.5 Give names for the following substituted alkanes :
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(H 3 C) 3 C CH(CH 3 ) 2 (a) (H 3 C) 2 HCH 2 C H 3 C H 3 C(H 2 C) 2 H 2 C (b) (c) Cl CH 3 CH 3 Cl OH OH C(CH 3 ) 3 (d) (e) (f) Answer: (a) 1- t -butyl-2-isopropylcyclopentane (b) 1-isobutyl-2-methylcyclohexane (c) butylcyclohexane (d) 1-chloro-2,4-dimethylcyclohexane (e) 2-chlorocyclopentanol (f) 3- t -butylcyclohexanol 4.6 Give names for each of the following bicyclic alkanes: (a) (b) (c) (d) (e) Cl Cl (f) Write the structure of a bicyclic compound that is an isomer of bicycl0[2,2,0]hexane and give its names. Answer:
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(a) 2-Chlorobicyclo[1,1,0]butane (b) Bicyclo[3,2,1]octane (c) Bicyclo[2,1,1]hexane (d) 2-Methylbicyclo[2,2,2]octane] (e) Bicyclo[3,1,0]hexane bicyclo[2,1,1]hexane 4.7 Give IUPAC names for the following alkenes: (a) (b) (c) (d) (e) (f) OH OH Cl Answer: (a) trans -3-Heptene (b) 2,5-Dimethyl-2-octene (c) 4-Ethyl-2-methyl-1-hexene (d) 3,5-Dimethylcyclohexene (e) 4-Methyl-4-pentene-2-ol (f) 2-Chloro-3-methyl-3-cyclohexen-1-ol 4.8 Write structure formula for the following: (a) cis -3-octene (b) trans -2-hexene (c) 2,4-dimethyl-2-pentene (d) trans -1-chloro-2-butane Cl
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(e) 4,5-dibromo-1-pentene Br Br (f) 1,3-dimethylcyclohexene (g) 3,4-dimethylcyclopentene (h) Vinylcyclopentane (i) 1,2-dichlorocyclohextene Cl Cl (j) trans -1,4-dichloro-2-pentene Cl Cl 4.9 Give the structures and IUPAC names for all the alkynes with the formula C 6 H 10 .
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This note was uploaded on 02/23/2010 for the course CHEM 101 taught by Professor Smith during the Spring '10 term at Duke.

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4_all_ - 4.1 Write condensed structural formulas for all of...

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