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Solutions_Manual_for_Organic_Chemistry_6th_Ed 453

Solutions_Manual_for_Organic_Chemistry_6th_Ed 453 - cAn ºe...

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19-28 Use a large excess of ammonia to avoid multiple alkylations of each nitrogen. Br + NH3 __ __ NH 2 19-29 o (a) �N: o o BrCH2Ph .. excess o C< N-CII2Ph o o NH2NH2 .. !l H2NCH2Ph (b ) v -- t Br(CH2hCH3 c< NH2NH2 - I N - (CH 2)sCH3 H2N(CH2)sCH3 :::-. .. !l o o ( c ) N : o o o Br(CH2hCOO- ---- -4 .. _ I N - (CH 2hCOO- must use anion :: :-. .. to avoid protonating 0 the phthalimide anion 1) NH2NH2 ' !l ... 2) H+ 19-30 Assume that LiAIH4 or Hz/catalyst
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Unformatted text preview: cAn ºe used ÆÑTeÒÀhAÑgeAºlyÓ ·hC¹2Br ± NAN3 ± PhC¹2N3 ¹2 PhC¹2N¹2 (a± ·T µ (b ) ² Ô ³ C = 1) LÆÎl¸4 • ´ Õ2 V v 2) ¹20 (À½ 0 µ OH 1) LIÎй4 ² 2) ¹20 ÖsCl . Oh py×dÆne Ø O Ös OR 0 ¶ OH S O C l 2 µ Ù NH2 o · Cl -Ú ÛÜsÝ Þ CßN FàoË ác½ 1± LÍÎй4 ³ 2² ¸20 N¹3 ´ + NaN3 â N3 o ¸ Nã2 LÍÎä¹4 ¹ ³² ¹2å æ ç2 èÍÎé¹4 ê NH2 ² ³² ¸2å 448 H2N²C³l´coOµ...
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