Reduction Of Amide - The Student Room

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Watch12 years agoReduction of amideElynQuestion : Treat CH3CONH2 with LiAlH4 in dry ether followed by the treatment of water produces__________. A) CH3CH(OH)NH2. B) CH3CH2NH2The answer is A or B?Appreciate your reply ^_^This was posted from The Student Room's iPhone/iPad App0ReportReply 112 years agoDoglamlico16Original post by ElynQuestion : Treat CH3CONH2 with LiAlH4 in dry ether followed by the treatment of water produces__________. A) CH3CH(OH)NH2. B) CH3CH2NH2The answer is A or B?Appreciate your reply ^_^This was posted from The Student Room's iPhone/iPad AppI'm going with C - Summer Holidays Why are you doing work, might I ask? 0ReportReply 212 years agoElynOPPreparing for my exam This was posted from The Student Room's iPhone/iPad App0ReportReply 312 years agoNutterFrutterOriginal post by ElynQuestion : Treat CH3CONH2 with LiAlH4 in dry ether followed by the treatment of water produces__________. A) CH3CH(OH)NH2. B) CH3CH2NH2The answer is A or B?Appreciate your reply ^_^This was posted from The Student Room's iPhone/iPad AppB, you get an amine.0ReportReply 412 years agoElynOPI see.Nthank youThis was posted from The Student Room's iPhone/iPad App0ReportReply 512 years agothegodofgod19Don't you get A, as the carbonyl group is reduced to a primary alcohol group via nucleophilic addition.0ReportReply 612 years agoTiTo207Original post by thegodofgodDon't you get A, as the carbonyl group is reduced to a primary alcohol group via nucleophilic addition.I agree, except it's a secondary alcohol =PThis was posted from The Student Room's iPhone/iPad App0ReportReply 712 years agothegodofgod19Original post by TiTo20I agree, except it's a secondary alcohol =PThis was posted from The Student Room's iPhone/iPad AppI'm pretty sure it's a primary alcohol.A secondary alcohol: R1-CH(OH)-R2, where both R groups contain a carbon group. In this case, one of the R groups is an amine, group, meaning the alcohol is primary, not secondary (AFAIK).0ReportReply 812 years agoNutterFrutterOriginal post by thegodofgodDon't you get A, as the carbonyl group is reduced to a primary alcohol group via nucleophilic addition.Isn't this only in aldehydes and ketones?0ReportReply 912 years agothegodofgod19Original post by NutterFrutterIsn't this only in aldehydes and ketones?I think it applies to all organic compounds 0ReportReply 1012 years agoThat Bearded Man22Original post by TiTo20I agree, except it's a secondary alcohol =PThis was posted from The Student Room's iPhone/iPad AppYou can oxidise a secondary alcohol, it's the tertiary that cannot be oxidised. Thus you should be able to reduce a keto- group into a hydroxy group no?0ReportReply 1112 years agoEierVonSatan21Reduction of an amide with LAH gives an amine.A carbon attached to both an OH group and a NH2 group is a functional group called a hemiaminal.1ReportReply 1212 years agoThat Bearded Man22If it's a straight reduction, why do you add water and what effect does that have?BTW I thought A, reduction of an amide = amine, but surely in excess the C=O is reduced also?0ReportReply 1312 years agoillusionz20Original post by thegodofgodDon't you get A, as the carbonyl group is reduced to a primary alcohol group via nucleophilic addition.Original post by TiTo20I agree, except it's a secondary alcohol =PThis was posted from The Student Room's iPhone/iPad AppOriginal post by That Bearded ManIf it's a straight reduction, why do you add water and what effect does that have?BTW I thought A, reduction of an amide = amine, but surely in excess the C=O is reduced also?The first step of the mechanism is that the nucleophile (LiAlH4) does attack the carbonyl group, as that is where the amide is electrophilic (albeit weakly due to the donation by the nitrogen lone pair). This forms an sp3 carbon centre (all single bonds), with one R group, one H, an NR2 and the O- (which is in reality coorinately bonded to the aluminium). This intermediate collapses to form an imine (the N analogue of a ketone) and kicks out the O-Al species. This imine is also electrophilic, and is attacked by another equivalent of LiAlH4 to produce the amine.(edited 12 years ago)0Report

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