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Organic Chemistry Ch. 6 - Aldehydes and Ketons I
MCAT
7
Organic Chemistry
Undergraduate 2
05/30/2016

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Term
Are aldehydes or ketones generally more reactive toward nucleophiles?
Definition
aldehydes because they have less steric hindrance and few electron donating alkyl groups
Term
What happens when a nucleophile reacts with aldehydes/ketones?
Definition
the nucleophile attacks the carbonyl carbon and breaks the pi bond it has with the oxygen pushing the electrons onto the oxygen; if there is a good leaving group (there isn't in ketones or aldehydes typically) the oxygen will accept a proton and that is that, otherwise the leaving group will go and the double bond will reform
Term
geminal diol
Definition
  • 1,1-diol (alcohol)
  • forms from aldehydes or ketones in the presence of water which attacks the carbonyl carbon
Term
hemiacetal or hemiketal
Definition

when one equivalent of alcohol reacts with an aldehyde or a ketone; the carbonyl carbon is then bonded to an alcohol and an oxygen (the oxygen is bound to the rest of its original alcohol structure)

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Term
acetal or ketal
Definition

formed when aldehydes or ketones are reacted with two equivalents of alcohol; act as good protecting groups; converted back with aqueous acid and heat

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Term
What is an imine and how are they produced?
Definition
a compound with an nitrogen atom double-bonded to a carbon atom formed when ammonia adds to a carbonyl carbon and water is lost; hydrazine, semicarbazide and hydroxylamine are ammonia derivates and react with aldehydes and ketones in the same way
Term
hydrogen cyanide
Definition
common nucleophile; when reacted with aldehydes and ketones they form cyanohydrins (the carbonyl carbon bound now to an alcohol and -CN)
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