1559T_ch13_247-25811/03/0520:12Pa9e255 EQA Solufionsto Problems255 CH ⊕ asistent with it the doubly deprotonated ethyne 43. →CH2=CHMgB ,人人 上H0 人 ,CH OH OH 人入个 CH)CO-K".CHCOH 上悠N (g) (h) (i) 41. (a) (b) 42. Ca2
:CqC: , a calcium salt of ethyne, is consistent with its reaction with water to form HCqCH. One could call this material “calcium acetylide” or, perhaps “ethynediylcalcium,” with the “di” referring to the doubly deprotonated ethyne. 43. 44. (CH3)3CO K
, (CH3)3COH HO Cl HO HO 1. Br2, CCl4, 2. NaNH2, NH3 PCC, CH2Cl2 product LiNH2, NH3 H2, Lindlar catalyst, CH3CH2OH HBr (1 equiv) Mg, THF HC CLi HC CH CH2 CHBr CH2 CHMgBr OH OH O 1. 2. H
, H2O O 1. 2. H
, H2O R3P, 100C Br
1% Pd(OCCH3)2 O Br COCH3
R3P, 100C O COCH3 O 1% Pd(OCCH3)2 O product H2, Pd-BaSO4, quinoline, CH3CH2OH 1. HC CLi, THF 2. H
, H2O,  O C CH THF HB 2 C CH
( ( 2 ( ( product H2O2, OH C C H H B HC CCHCH3 product H2, Pd-BaSO4, quinoline, CH3CH2OH 1. BH3, THF 2. H2O2, HO OH H2C CHCHCH3 OH Solutions to Problems • 255 1559T_ch13_247-258 11/03/05 20:12 Page 255