05_ - P1: PBU/OVY P2: PBU/OVY JWDD052-05...

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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-05 JWDD052-Solomons-v1 March 15, 2007 19:13 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), and (f) 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 (e) ( 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 64
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-05 JWDD052-Solomons-v1 March 15, 2007 19:13 STEREOCHEMISTRY: CHIRAL MOLECULES 65 (g) (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 (h) ( 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 5.6 (a) Two in each instance. and l l C l Cl H C HB r H C and r l C Cl
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-05 JWDD052-Solomons-v1 March 15, 2007 19:13 66 STEREOCHEMISTRY: CHIRAL MOLECULES (b) Only one in each instance. Cl H H Cl C Br H H Cl C Any other tetrahedral arrangements will be superposable on one or the other of the above. (c) Three: HF Cl Br C F H Cl Br C and Cl Br H F C (d) Two: and F H Br Cl C F H Cl Br C 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 de±ned by the page is a plane of symmetry. (a) H H 3 C H 3 C F C (b) H H 3 C CH 2 CH 3 H 3 C C (f) H CH 3 CH 3 CH 2 CH 3 CH 2 C 5.9 ( S ) F Br H Cl C ( R ) F Br H Cl C 5.10 (c) (1) is ( S ) (2) is ( R ) (d) (1) is ( S ) (2) is ( R ) (e) (1) is ( S ) (2) is ( R ) (g) (1) is ( S ) (2) is ( R ) (h) (1) is ( S ) (2) is ( R )
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-05 JWDD052-Solomons-v1 March 15, 2007 19:13 STEREOCHEMISTRY: CHIRAL MOLECULES 67 5.11 ±Cl OH SH > H > > ±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) 5.12 (a) ( S ) (b) ( R ) (c) ( S ) 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. 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
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P1: PBU/OVY P2: PBU/OVY QC: PBU/OVY T1: PBU Printer: Hamilton JWDD052-05 JWDD052-Solomons-v1 March 15, 2007 19:13 68 STEREOCHEMISTRY: CHIRAL MOLECULES 5.17 (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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05_ - P1: PBU/OVY P2: PBU/OVY JWDD052-05...

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