Solutions_Manual_for_Organic_Chemistry_6th_Ed 226

Solutions_Manual_for_Organic_Chemistry_6th_Ed 226 - 1 0-26...

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10-26 continued (c) ~ NaBH4 ~ 1) LiAIH4 .. OR .. CH30H 2) H30 + 0 OH (d) W O NaBH4 C�X:f LiAlH4 will NOT give the desired .. product. LiAIH4 will also reduce the CH30H ester in addition to the ketone. 0 OH 10-27 Approximate pKa values are shown below each compound. Refer to text Tables 1-5, 9-2, and 10-3, and Appendix 5 at the back of the text. CH3S03H > CH3COOH > CH3SH > CH30H > CH3C:: CH > CH3NH2 > CH3CH3 < 0 4.74 "" 10.5 15.5 25 "" 35 50 most acidic 10-28 (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 OR HBr Br ROOR NBS - -- -l ..
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