372 ALCOHOLS, DIOLS. AND 15.19(a) All the carbon-carbon disconnections are equivalent. CH Hc--o□>cH3+cHcH H Acetone The synthesis via a grignard reagent and acetone is diethyl ether 2.HO+ (CH3), COH Methyl (b) An alternative route to tert-butyl alcohol is addition of a grignard reagent to an ester. Esters react with 2 moles of Grignard reagent. Thus, tert-butyl alcohol may be formed by reacting nethyl acetate with 2 moles of methylmagnesium iodide. Methyl alcohol is formed as a by product of the reaction. 2CH, Mgl + CH,COCH3 2 H,0+. diethyl C-OH t CHOH Methy magnesium Methyl acetate tert-Butyl alcohol Meth 15.20(a) All of the primary alcohols having the molecular formula CsHno may be prepared by redu on of aldehydes. The CHCH,, CH 1. LiAlH4- diethyl et CH3 CH2CHCH,CH,C 1-Pentanol LiAIHg, diethyl ether CHCH, CHCH 2.H,O CHa CH,CHCH,OH CH 2-Methylbutanal 2-Methyl-1-butanol 1. LiAlH4, diethyl eth (CH,),CHCH,CH (CH3), CHCH,CH,OH 3-Methylbutanal 3. Me 1. LiAIHa, diethyl ether (CH3),CCH (CH3)CCH,OH 2-Dimethylpropanal 2. 2-Dimethyl-1-propanol Back Forward Main Menu TOC Study Guide Toc Student OLC MHHE Website15.19 (a) All the carbon–carbon disconnections are equivalent. The synthesis via a Grignard reagent and acetone is (b) An alternative route to tert-butyl alcohol is addition of a Grignard reagent to an ester. Esters react with 2 moles of Grignard reagent. Thus, tert-butyl alcohol may be formed by reacting methyl acetate with 2 moles of methylmagnesium iodide. Methyl alcohol is formed as a by￾product of the reaction. 15.20 (a) All of the primary alcohols having the molecular formula C5H12O may be prepared by reduc￾tion of aldehydes. The appropriate equations are 1. LiAlH4, diethyl ether 2. H2O 2,2-Dimethylpropanal O (CH3)3CCH 2,2-Dimethyl-1-propanol (CH3)3CCH2OH 1. LiAlH4, diethyl ether 2. H2O 3-Methylbutanal O (CH3)2CHCH2CH 3-Methyl-1-butanol (CH3)2CHCH2CH2OH 2-Methyl-1-butanol 1. LiAlH4, diethyl ether 2. H2O 2-Methylbutanal CH3CH2CHCH O CH3 CH3CH2CHCH2OH CH3 CH3CH2CH2CH2CH2OH 1-Pentanol 1. LiAlH4, diethyl ether 2. H2O Pentanal CH3CH2CH2CH2CH O Methylmagnesium Methyl acetate tert-Butyl alcohol iodide C CH3 CH3 OH CH3 CH3COCH3 O Methyl alcohol 2CH3MgI CH3OH 1. diethyl ether 2. H3O CH3Br Methylmagnesium bromide CH3MgBr (CH3)3COH Mg diethyl ether 1. CH3CCH3 2. H3O O Methyl tert-Butyl alcohol bromide CH3CCH3 Acetone C CH3 H3C OH CH3 O CH3 372 ALCOHOLS, DIOLS, AND THIOLS Back Forward Main Menu TOC Study Guide TOC Student OLC MHHE Website