Solutions_Manual_for_Organic_Chemistry_6th_Ed 199

Solutions_Manual_for_Organic_Chemistry_6th_Ed 199 - 9 -6...

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Unformatted text preview: 9 -6 H-C:::C-H NaNH2 H-C:::C : Na+ CH3CH2Br H-C:::C-CH2CH3 � NaNH2 CH3(CH2)S-C:::C-CH2CH3 CH3(CH2)SBr Na+ :C:::C-CH2CH3 (a) H-C:::C-H NCaNH2 H3CH2CH2CH2Br H-C:::C-CH2CH2CH2CH3 (b) H-C:::C-H NCaNH2 H-C:::C-CH2CH2CH3 NCaNH2.. CH3-C:::C-CH2 2CH3 H3I H3CH2CH2Br aNH2 (c) H-C:::C-H 2) NCH3CH2Br.. H-C:::C-CH2CH3 NCaNH2 CH3CH2-C:::C-CH2CH3 H3CH2Br (d) cannot be synthesized by an reaction-would require attack on a alkyl halide r/ 2° _��HCH2CH3 CH3-C:::C : Na;+ C strust benucleophiorder CH3 fr CH3-C:::C-CHCH2CH3 Cnot practical H3 m ong second le low yields; (e) H-C:::C-H NCaNH2 CH3-C:::C-H NaNH2 H3I BrCH2CHCH3 CH3-C::: C-CH2CHCH3 CH3 CH3 H-C:::C-H NBaNH2 H-C :::: C-?H2 r(CH2)8Br Br� � NaNH2 Na+ -,C-C-CH2 H2C-C:::C-CH2 = � Br Intlramolinetramolcyclizaatiand of largeennolecular.�e solution so the last displacement cular ecul r on not int rings must be carried out in dilut wi be .. • .. 9 -7 1) 2) .. 1) 1) 2) 1) • 2) CH 1) 2) • S N2 20 + I 1) 2) .. 1) 2) .. I I (f) 1) 2) .. ..!--... - .. r'. �. S N2 9 -8 (a) H-C:::C-H NaNH2 H20 H-C:::C-CH20H H2C=O 1) 2) .. ----l.� 192 ...
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