Chapter_23 - P1: PBY JWDD052-23 JWDD052-Solomons-v3...

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P1: PBY Printer: Hamilton JWDD052-23 JWDD052-Solomons-v3 May 4, 2007 14:19 23 LIPIDS SOLUTIONS TO PROBLEMS 23.1 (a) There are two sets of enantiomers, giving a total of four stereoisomers: (CH 2 ) 7 H Br + erythro threo and + C (CH 2 ) 5 CH 3 C CO 2 H HB r (CH 2 ) 7 Br H (CH 2 ) 5 CH 3 CO 2 H Br H (CH 2 ) 7 r (CH 2 ) 5 CH 3 CO 2 H Br H (CH 2 ) 7 Br H C (CH 2 ) 5 CH 3 C CO 2 H r C C C C (b) CH 3 (CH 2 ) 5 HH (CH 2 ) 7 CO 2 H (CH 2 ) 7 r (CH 2 ) 5 CH 3 CO 2 H Br H (CH 2 ) 7 Br H (CH 2 ) 5 CH 3 C CO 2 H r C + Br 2 CH 3 (CH 2 ) 5 H (a) (a) (b) (b) Br + Br H (CH 2 ) 7 CO 2 H C CH 3 (CH 2 ) 5 H Br C CH 3 (CH 2 ) 5 Br Br H H (CH 2 ) 7 CO 2 H ( ± )- threo -9,10-Dibromohexadecanoic acids C C Br H (CH 2 ) 7 CO 2 H C C C C C C 542
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P1: PBY Printer: Hamilton JWDD052-23 JWDD052-Solomons-v3 May 4, 2007 14:19 LIPIDS 543 Formation of a bromonium ion at the other face of palmitoleic acid gives a result such that the threo enantiomers are the only products formed (obtained as a racemic modi±cation). The designations erythro and threo come from the names of the sugars called erythrose and threose (Section 22.9A). 23.2 Zingiberene (a sesquiterpene) β -Selinene (a sesquiterpene) Squalene (a triterpene) Caryophyllene (a sesquiterpene) (a,b) 23.3 (a) (b) Myrcene Limonene HH O + + + ++ + O O O H O H O + O O O H O O H O O O (1) O 3 (2) Zn, HOAc (1) O 3 (2) Zn, HOAc + O H O (c) α -Farnesene (see Section 23.3) O (1) O 3 (2) Zn, HOAc O H H H H
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P1: PBY Printer: Hamilton JWDD052-23 JWDD052-Solomons-v3 May 4, 2007 14:19 544 LIPIDS (d) + Geraniol (see Section 23.3) (e) Squalene (see Section 23.3) + O H H H O OH H O O + + O O H O O 2 4 O (1) O 3 (2) Zn, HOAc (1) O 3 (2) Zn, HOAc 23.4 (a) (c) (b) (d) ( + further oxidation products) ( + rearranged products) OH O + CO 2 Cl Cl OH 23.5 Br 2 in CCl 4 or KMnO 4 in H 2 O at room temperature. Either reagent would give a positive result with geraniol and a negative result with menthol. 23.6 5 α Series (e) H H (e) H H (a) (a) H (a) H (a) H (a) H (a) (e) H (e) H CH 3 CH 3 (e) H (a) H (a) H (a) (a) H H (a) H (e) H (a) H H (e) H (e)
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P1: PBY Printer: Hamilton JWDD052-23 JWDD052-Solomons-v3 May 4, 2007 14:19 LIPIDS 545 (a) H (e) H (e) H H (e) H (a) H (a) H (a) H (a) H (a) H (a) (a) H CH 3 CH 3 (a) H (e) H (a) H (e) H H (e) H (a) H (e) H (e) H (a) 5 β Series 23.7 3 α -Hydroxy-5 α -androstan-17-one (androsterone) 17 α -Ethynyl-17 β -hydroxy-5(10)-estren-3-one (norethynodrel) (a) (b) HO H H H O H H 3 C H 3 C H H OH O H CH C H 3 C 23.8 Absolute configuration of cholesterol (5-cholesten-3 β -ol) HO H H H H H 3 C H 3 C CH 3 23.9 Estrone and estradiol are phenols and thus are soluble in aqueous sodium hydroxide. Ex- traction with aqueous sodium hydroxide separates the estrogens from the androgens.
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This note was uploaded on 09/10/2008 for the course CHE 321 taught by Professor Fowler/sampson during the Spring '08 term at SUNY Stony Brook.

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Chapter_23 - P1: PBY JWDD052-23 JWDD052-Solomons-v3...

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