05+ - P1: PBU/OVY JWCL234-05 P2: PBU/OVY QC: PBU/OVY T1:...

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES 5 STEREOCHEMISTRY: CHIRAL MOLECULES SOLUTIONS TO PROBLEMS 5.1 (a) Achiral (b) Achiral (c) Chiral (d) Chiral (e) Chiral (f) Chiral (g) Chiral (h) Achiral 5.2 (a) Yes (b) No (c) No 5.3 (a) They are the same molecule. (b) They are enantiomers. 5.4 (a), (b), (e), (g), and (i) do not have chirality centers. (c) ( 1 ) CH 3 CH 3 CH 2 C HC l ( 2 ) CH 3 CH 3 CH 2 H Cl C (f) ( 1 ) CH 3 CH 2 CH 3 CH 2 HB r ( 2 ) CH 3 CH 2 CH 3 CH 2 H Br (d) ( 1 ) CH 3 CH 3 CH 2 CH 2 OH H HOCH 2 ( 2 ) CH 3 CH 3 CH 2 H C C C C 66
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES STEREOCHEMISTRY: CHIRAL MOLECULES 67 (h) (1 ) CH 2 CH 3 CH 2 CH 3 CH 2 HC H 3 ( 2 ) CH 2 CH 3 CH 2 CH 3 CH 2 H H 3 C (j) ( 1 ) CH 3 CH 3 CH 2 H 2 Cl ( 2 ) CH 3 CH 3 CH 2 H ClCH 2 C C C C 5.5 (a) Limonene (b) N N H O O O O Thalidomide * ( R )( S ) H ( S R ) * H N O O N H O O H N O O N H O O H
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES 68 STEREOCHEMISTRY: CHIRAL MOLECULES 5.6 * OH OH O * O OH HO * * OH OH HO OO HO * * * * * OH HO (a) (b) (c) (d) H 5.7 The following items possess a plane of symmetry, and are, therefore, achiral. (a) A screwdriver (b) A baseball bat (ignoring any writing on it) (h) A hammer 5.8 In each instance below, the plane deFned by the page is a plane of symmetry. (a) H H 3 C H 3 C ± C (b) H H 3 C CH 2 CH 3 H 3 C C H H CH 3 CC CH 3 (e) (g) H CH 3 CH 3 CH 2 CH 3 CH 2 C H CH 3 CH 3 CH 2 CH 3 (i) 5.9 ( S ) ± Br H Cl C ( R ) ± Br H Cl C 5.10 (c) (1) is ( S ) (2) is ( R ) (d) (1) is ( S ) (2) is ( R )
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES STEREOCHEMISTRY: CHIRAL MOLECULES 69 (f) (1) is ( S ) (2) is ( R ) (h) (1) is ( S ) (2) is ( R ) (j) (1) is ( S ) (2) is ( R ) 5.11 ±Cl OH SH > H > OH > > ±CH 2 Br 2 Cl > 2 OH > 3 > OH CHO > CH 3 > H > C(CH 3 ) 3 > CH(CH 3 ) 2 H > CH CH 2 > OCH 3 > N(CH 3 ) 2 CH 3 H >> (a) (b) (c) (d) (e) OPO 3 H 2 > CHO H > (f) 5.12 (a) ( S ) (b) ( R ) (c) ( S ) (d) ( R ) 5.13 (a) Enantiomers (b) Two molecules of the same compound (c) Enantiomers 5.14 ( S )-( + )-Carvone H O ( R )-( )-Carvone H O 5.15 (a) Enant. Excess = observed speciFc rotation speciFc rotation of pure enantiomer × 100 = + 1 . 151 + 5 . 756 × 100 = 20 . 00% (b) Since the ( R ) enantiomer (see Section 5.8C) is + , the ( R ) enantiomer is present in excess.
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES 70 STEREOCHEMISTRY: CHIRAL MOLECULES 5.16 (a) ( S )-Methyldopa HO OH CH 2 NH 2 CH 3 C HO O (b) ( S )-Penicillamine NH 2 H CH 3 CH 3 SH C OH C O C (c) ( S )-Ibuprofen CH 3 CH 2 CH 3 H C H OH CH 3 C C O C 5.17 HO H ( R ) configuration 5.18 The conFguration is R at both chirality centers. ( R ) ( R ) O N O 5.19 (a) Diastereomers. (b) Diastereomers in each instance. (c) No, diastereomers have different melting points. (d) No, diastereomers have different boiling points. (e) No, diastereomers have different vapor pressures.
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Bind Rite JWCL234-05 JWCL234-Solomons-v1 December 8, 2009 21:33 CONFIRMING PAGES STEREOCHEMISTRY: CHIRAL MOLECULES 71 STUDY AID An Approach to the Classification of Isomers Do the compounds have the same molecular formula?
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This note was uploaded on 10/20/2011 for the course CHEMISTRY ES110 taught by Professor Te.li during the Spring '11 term at Central Texas College.

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05+ - P1: PBU/OVY JWCL234-05 P2: PBU/OVY QC: PBU/OVY T1:...

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