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4Nomenclature and Conformations of Alkanes P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 4 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES SOLUTIONS TO PROBLEMS 4.1 or or CH3(CH2)5CH3 (CH3)2CHCH2CH2CH2CH3 Heptane 2-Methylhexane or or CH3CH2CH(CH3)CH2CH2CH3 (CH3)3CCH2CH2CH3 3-Methylhexane 2,2-Dimethylpentane or or (CH3CH2)2C(CH3)2 (CH3)2CHCH(CH3)CH2CH3 3,3-Dimethylpentane 2,3-Dimethylpentane or or (CH ) CHCH CH(CH ) 3 2 2 3 2 (CH3CH2)3CH 2,4-Dimethylpentane 3-Ethylpentane or (CH3)3CCH(CH3)2 2,2,3-Trimethylbutane 47 CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 48 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 4.2 (d); it represents 3-methylpentane 4.3 CH3CH2CH2CH2CH2CH3 hexane 4.4 (a,b) 2-Methylheptane 3-Methylheptane 4-Methylheptane 2,2-Dimethylhexane 2,3-Dimethylhexane 2,4-Dimethylhexane 2,5-Dimethylhexane 3,3-Dimethylhexane 3,4-Dimethylhexane 3-Ethylhexane 2,2,3-Trimethylpentane 2,2,4-Trimethylpentane 2,3,3-Trimethylpentane 2,3,4-Trimethylpentane 3-Ethyl-2-methylpentane 3-Ethyl-3-methylpentane 2,2,3,3-Tetramethylbutane CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 49 4.5 (a) Pentyl 1-Methylbutyl 1-Ethylpropyl 2-Methylbutyl 3-Methylbutyl 1,2-Dimethylpropyl 1,1-Dimethylpropyl (b) See the answer to Review Problem 4.1 for the formulas and names of C7H16 isomers. 4.6 (a) Cl Cl 1-Chlorobutane 1-Chloro-2-methylpropane Cl Cl 2-Chlorobutane 2-Chloro-2-methylpropane Br (b) Br 1-Bromopentane 1-Bromo-3-methylbutane Br Br 2-Bromopentane 1-Bromo-2-methylbutane Br Br 3-Bromopentane 2-Bromo-3-methylbutane Br Br 1-Bromo-2,2-dimethylpropane 2-Bromo-2-methylbutane CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 50 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES (a) 4.7 OH OH 1-Butanol 2-Methyl-1-propanol OH OH 2-Butanol 2-Methyl-2-propanol (b) OH OH 1-Pentanol 3-Methyl-1-butanol OH OH 2-Pentanol 2-Methyl-1-butanol OH OH 3-Pentanol 3-Methyl-2-butanol OH OH 2,2-Dimethyl-1-propanol 2-Methyl-2-butanol 4.8 (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 4.9 (a) 2-Chlorobicyclo[1.1.0]butane (e) 2-Methylbicyclo[2.2.2]octane (b) Bicyclo[3.2.1]octane (f) Bicyclo[3.1.0]hexane or (c) Bicyclo[2.1.1]hexane (d) 9-Chlorobicyclo[3.3.1]nonane bicyclo[2.1.1]hexane CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 51 4.10 (a) trans-3-Heptene (d) 3,5-Dimethylcyclohexene (b) 2,5-Dimethyl-2-octene (e) 4-Methyl-4-penten-2-ol (c) 4-Ethyl-2-methyl-l-hexene (f) 2-Chloro-3-methylcyclohex-3-en-1-ol 4.11 (a) (b) (c) Br Br (d) Cl (e) (f) Br Cl (g) (h) (i) Cl Cl (j) Cl 4.12 1-Hexyne 2-Hexyne3-Hexyne 3,3-Dimethyl- 1-butyne 3-Methyl-1-pentyne 4-Methyl-1-pentyne 4-Methyl-2-pentyne CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 52 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 4.13 H3C H3C H3C CH3 CH H H3C H 3 H3C H H H H H H H CH3 CH3 CH3 CH3 H CH3 H H H H Potential energy Potential H3C H3C H3C H3C H3C H H CH3 H3C CH3 H3C H H H H H 0° 60° 120° 180° 240° 300° 360° Rotation G◦ −7600 J 4.14 log Keq = = = 1.32 −2.303RT (−2.303)(8.314JK−1)(298 K) Keq = 21.38 Let e = amount of equatorial form and a = amount of axial form e then, K = = 21.38 eq a e = 21.38a 21.38a % e = × 100 = 95.5% a + 21.38a Br Br 4.15 (a)H H Cl H (b) Br Cl Cl HCl Br (cis) (trans) (cis) (trans) (c) No 4.16 (a-d) More stable because Less stable because larger group is equatorial larger group is axial and so preferred at equilibrium CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 53 F Br 4.17 Cl F Br Cl all equatorial all axial (more stable) (less stable) 4.18 (a,b) Less stable because the large More stable because the large tert-butyl group is axial tert-butyl group is equatorial (more potential energy) (less potential energy) 4.19 H2 H2 Pd, Pt or Ni Pd, Pt or Ni pressure pressure H2 Pd, Pt or Ni pressure H2 Pd, Pt or Ni pressure 4.20 (a) C6H14 = formula of alkane C6H12 = formula of 2-hexene H2 = difference = 1 pair of hydrogen atoms Index of hydrogen deficiency = 1 (b) C6H14 = formula of alkane C6H12 = formula of methylcyclopentane H2 = difference = 1 pair of hydrogen atoms Index of hydrogen deficiency = 1 (c) No, all isomers of C6H12, for example, have the same index of hydrogen deficiency. (d) No CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 54 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES (e) C6H14 = formula of alkane C6H10 = formula of 2-hexyne H4 = difference = 2 pairs of hydrogen atoms Index of hydrogen deficiency = 2 (f) C10H22 (alkane) C10H16 (compound) H6 = difference = 3 pairs of hydrogen atoms Index of hydrogen deficiency = 3 The structural possibilities are thus 3 double bonds 1 double bond and 1 triple bond 2 double bonds and 1 ring 1 double bond and 2 rings 3 rings 1 triple bond and 1 ring 4.21 (a) C15H32 = formula of alkane C15H24 = formula of zingiberene H8 = difference = 4 pairs of hydrogen atoms Index of hydrogen deficiency = 4 (b) Since 1 mol of zingiberene absorbs 3 mol of hydrogen, one molecule of zingiberene must contain three double bonds. (We are told that molecules of zingiberene do not contain any triple bonds.) (c) If a molecule of zingiberene has three double bonds and an index of hydrogen deficiency equal to 4, it must have one ring. (The structural formula for zingiberene can be found in Review Problem 23.2.) 4.22 CH3O molecular formula C10H16O2 O C10H22 = formula for alkane C10H16 = formula for unsaturated ester (ignoring oxygens) H6 = difference = 3 pairs of hydrogen atoms IHD = 6 CH3O molecular formula C10H18O2 Ο C10H22 = formula for alkane C10H18 = formula for hydrogenation product (ignoring oxygens) H4 = difference = 2 pairs of hydrogen atoms IHD = 4 CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 55 Nomenclature and Isomerism Cl Br 4.23 (a) (b) Cl (c) (d) Cl Cl (e) (f) H H H CH3 (g) (h) CH3 CH3 CH3 H OH OH (i) (j) (k) (l) OH (m) or (n) (o) 4.24 (a) 3,3,4-Trimethylhexane (b) 2,2-Dimethyl-1-butanol (c) 3,5,7-Trimethylnonane (d) 3-Methyl-4-heptanol (e) 2-Bromobicyclo[3.3.1]nonane CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 56 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES (f) 2,5-Dibromo-4-ethyloctane (g) Cyclobutylcyclopentane (h) 7-Chlorobicyclo[2.2.1]heptane 4.25 The two secondary carbon atoms in sec-butyl alcohol are equivalent; however, there are three five-carbon alcohols (pentyl alcohols) that contain a secondary carbon atom. H3C CH3 4.26 (a)CH3 C C CH3 (b) H3C CH3 Cyclohexane 2,2,3,3-Tetramethylbutane CH3 (c) (d) CH3 Bicyclo[2.2.2]octane 1,1-Dimethylcyclobutane CH3 4.27 CH3 C CH2CHCH3 or 2,2,4-trimethylpentane CH3 CH3 CH3 CH3CH2 C CHCH3 or 2,3,3-trimethylpentane H3C CH3 CH3 CH3 C CHCH2CH3 or 2,2,3-trimethylpentane H3C CH3 4.28 Cyclopentane Methylcyclobutane cis-1,2-Dimethylcyclopropane trans-1,2-Dimethylcyclopropane1,1-Dimethylcyclopropane Ethylcyclopropane CONFIRMING PAGES P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-04 JWCL234-Solomons-v1 December 8, 2009 21:31 NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES 57 Cl H CH3 4.29 (a) (b) (c) (d) 4.30 S − A + 1 = N For cubane, S = 12 and A = 8. Thus 12 − 8 + 1 = N; N = 5 rings in cubane. 4.31 (a) (b) 4.32 A homologous series is one in which each member of the series differs from the one preceding it by a constant amount, usually a CH2 group. A homologous series of alkyl halides would be the following: CH3X CH3CH2X CH3(CH2)2X CH3(CH2)3X CH3(CH2)4X etc.
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