Solutions_Manual_for_Organic_Chemistry_6th_Ed 209

Solutions_Manual_for_Organic_Chemistry_6th_Ed 209 -...

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Unformatted text preview: 9 -27 (a) (d) C H3CH2-C::C -(CH2)4CH3 (b) (e) H3C-C::C-(CH2)4CH3 (c) (f) �' Br o- C::C-H CH3CH2-C:: C - CHCH2CH2CH3 C H3 I ( )I \ C::C-H ( g) C H3CH-C::C - (CH2hCH3 OH I (h) H3C \ I C::C-CHCH2CH3 H CH2CH3 C=C I H (i) H - C:: C - CH2 - C::C - CH2CH3 (j) H-C::C-CH=CH2 ( k) H-C::C -( CH3 H " 9 -28 (a) ethylmethylacetylene (b) phenyl acetylene 9-29 (a) 4-phenylpent-2-yne (b) 4,4-dibromopent-2-yne 9-30 (a) internal alkynes CH3 - C::C-CH2CH2CH3 C=CH2 , H (c) sec-butyl-n-propylacetylene (d) sec-butyl-t-butylacetylene (c) 2,6,6-trimethylhept-3-yne (d) (E)-3-methylhept-2-en-4-yne (e) 3-methylhex-4-yn-3-ol (f) cycloheptylprop-I-yne t erminal alkynes H - C::C - (CH2hCH3 acetylide ions C:: C - (CH2hCH3 h ex-2-yne CH3CH2 - C:: C - CH2CH3 h ex- l -yne H - C::C - CHCH2CH3 CH3 I - C:: C-CHCH2CH3 . C H3 I h ex-3-yne C H3-C::C-CHCH3 C H3 I 3-methylpent- l -yne H - C :: C-CH2CHCH3 CH3 I NaNH2 C::C-CH2CHCH3 CH3 CH3 C::C-C-CH3 . C H3 I I I 4-methylpent-2-yne 4-methylpent- l -yne CH3 H -C::C - C - CH3 CH3 I I 3,3-dimethylbut- l -yn (b) All four terminal alkynes will be deprotonated with sodium amide. 9 -3 1 CH3CH2-C H (R�-: �a b .C==CH H20 --• OH � e thchlorvynol " NH2 CH CH3CH2 - C-C-CH HC � " CHCI I I CHCl HC 202 ...
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