Solutions_Manual_for_Organic_Chemistry_6th_Ed 210

Solutions_Manual_for_Organic_Chemistry_6th_Ed 210 - 9-32...

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Unformatted text preview: 9-32 H-C:::C-H NaNH2 .. CH3(CH2hBr .. CHiCH2h-C::: C -H NaNH2 CH3(CH2h / \ (CH2)12CH3 I C=C H2 Lindlar catalyst H H muscalure 9-33 (a) Cl I CH2 = CCH2CH2CH3 \ ..1-----.. .. - CH3(CH2h -C::: C - (CH2) 12CH3 "1 CH3(CH2)12Br Cl I ( b) H3C-C-CH2CH2CH3 Cl H I ( c) CH3CH2CH2CH2CH3 H - <? - <? - CH2CH2CH3 B r Br B r Br I I (d) CH2 = CHCH2CH2CH3 o0 II II (e) C=C \ I Br CH2CH2CH3 0 CO2 + HO - C - CH2CH2CH3 II II \ I Br (f) (g) HO - C-C-CH2CH2CH3 Na+ - (h) (i) H2C = CHCH2CH2CH1 0 II (I) H - C - CH2CH2CH2CH3 G) 9 -34 (a) : C ::: C-CH2CH2CH3 Br 0 (k) H3C - C - CH2CH2CH3 H2O .. .. H3C - C -CH2CH3 Br Br I I NaNH2 1500 KOH 2 000 H-C:::C -CH2CH3 (b) H3C - C -CH2CH3 Br I I .. H3C-C::: C-CH3 (c) CH3CH2-C=C-H _ NaNH2 _ .. CH3CH2-C=C: CH3CH2 -C:: C -CH2CH2CH2CH3 H3C (d) \ � Na+ CH3CH2CH2CH2Br H I C=C I H CH2CH2CH3 B r2 --- Br B r CH3C -CCH2CH2CH3 • \ I I KOH 2000 .. C Cl4 HH I H3C -C::: C -CH2CH2CH3 this product could contain minor amounts of 3-hexyne from rearrangement H (e) \ H3C I C=C \ I H CH2CH2CH3 B r2 --- Br Br CH3C -CCH2CH2CH3 • I I C Cl4 HH I 2) H2O 203 1 ) NaNH2 1 500 .. H - C == C - CH2CH2CH2CH3 ...
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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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