Solutions_Manual_for_Organic_Chemistry_6th_Ed 226

Solutions_Manual_for_Organic_Chemistry_6th_Ed 226 - 1 0-26...

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Unformatted text preview: 1 0-26 continued (c) ~ 0 NaBH4 C H30H O NaBH4 CH30H .. .. ~ OH OR 1 ) LiAIH4 2) H30+ .. (d) 1 0-27 Approximate pKa values are shown below each compound. Refer to text Tables 1-5, 9-2, and 1 0-3, and Appendix 5 at the back of the text. CH3S03H > C H3COOH > C H3SH > C H30H > CH3C:: CH > C H3NH2 > C H3CH3 <0 4.74 "" 1 0.5 15.5 25 "" 35 50 most acidic 1 0-28 (a) 4-methylpentane-2-thiol (b) (Z)-2,3-dimethylpent-2-ene- l -thiol (" 1" is optional) (c) cyclohex-2-ene- l -thiol (" 1" is optional) 10-29 least acidic W 0 C�X:f OH LiAlH4 will NOT give the desired p roduct. LiAIH4 will also reduce the ester in addition to the ketone. � HB r ROOR ----l� .. OR � �o NBS � Br NaSH NaSH .. � Br ( see Problem 8-2) c .. � SH 3-methylbutane-I-thiol 2-butene-l-thiol (but-2-ene-l-thiol) � SH 1 0-30 Please refer to solution 1-20, page 12 of this Sol utions Manual. 1 0-3 1 (a) 5-methyl-4-n-propylheptan-2-01; 2° (b) 4-(I-bromoethyl)heptan-3-01; 2° (c) (E)-4,5-dimethylhex-3 -en-l-01; 1° (d) 3-bromocyclohex-3-en- l -01; 2° (" 1" is optional) (e) cis-4-chlorocyclohex-2-en-l-ol; 2° (" 1" is optional) (f) 6 -chloro-3-phenyloctan-3-01; 3° (g) (l-cyclopentenyl)methanol; 1° 1 0-32 (a) 4-chloro- l -phenylhexane- l ,5-diol (b) trans-cyclohexane-l,2-diol (c) 3-nitrophenol (d) 4-bromo-2-chlorophenol 219 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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