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Solutions_Manual_for_Organic_Chemistry_6th_Ed 199

Solutions_Manual_for_Organic_Chemistry_6th_Ed 199 - 9-6...

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9-6 H-C:: :C-H NaNH2 .. - H-C:::C: CH3(CH2)S -C:: :C-CH2CH3 9-7 1) NaNH2 CH3CH2Br Na+ H-C:: :C-CH2CH3 NaNH2 CH3(CH2)SBr .. Na+ :C:: :C-CH2CH3 .. (a) H-C:: :C-H 2) CH3CH2CH2CH2Br H -C:::C-CH2CH2CH2CH3 1 ) NaNH2 1 ) NaNH2 (b) H-C:: :C-H H-C:::C-CH CH CH .. CH -C:: :C-CH CH CH 2) CH3CH2CH2Br 2 2 3 2) CH3 I 3 2 2 3 1 ) NaNH2 1 ) NaNH2 (c) H-C:: :C-H .. H-C:::C-CH2CH3 CH3CH2-C:::C-CH2CH3 2) CH3CH2Br 2) CH3CH2Br (d) cannot be synthesized by an S N 2 reaction-would require attack on a 20 alkyl halide _ �� r/ 2 ° CH3-C:: :C: Na+ + CHCH2CH3 strong nucleophile; CH must be second
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