Solutions_Manual_for_Organic_Chemistry_6th_Ed 211

Solutions_Manual_for_Organic_Chemistry_6th_Ed 211 - 9 -34...

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Unformatted text preview: 9 -34 continued ( f) Hz L indlar catalyst Na .. W W �� cis (g) NH3 .. trans H z0 (h) HC:: C - CHzCHzCHzCH3 ___---i "� HZ S04 HgS04 [ I CH2 = H2CH2cH2cH3 unstable enol . 1 - H3C - CH2CH2CH2C H] � Br B r CH3C-CCH2CH2CH3 • this product could contain minor amounts of 3-hexyne from rearrangement I KOH ---J"� HH I 200° H3C - C:: C -CHzCH2CH3 major Hz H3C \ Lindlar •I c atalyst I \ CHzCH2CH3 9-35 Br � Br KOH .. 2 00° HC \ � + � f rom rearrangementcould contain 3-hexyne H I C =C H '-------.. only the terminal alkyne reacts with NaNH2 and acetone Y + OH j 2 � � o / J t t M ixtureA Mhture B OH CompoundD b.p. 1 40- 1 50°C under vacuum 204 J� � C ompoundC b.p. 80-84°C ...
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