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Ochem-CH21-COOHs
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Acyl phosphate
Nucleophilic Acyl Substitution Reaction
Nomenclature
An Sn2 reaction occurs in how many steps? A nucleophilic acyl substitution occurs in how many steps?
One. Two.
Describe the mechanism for an Sn2 reaction.
Describe the mechanism for a nucleophilic acyl substitution.
Backside displacement of the leaving group.
Tetrahedral intermediate.
In a nucleophilic acyl substitution reaction, ___ carbonyl groups are more reactive.
unhindered
In a nucleophilic acyl substitution reaction, ___ acyl compounds are more reactive.
strongly polarized
List the order of reactivty for acid chlorides, amides, esters, thioesters, and acid anhydrides.
Acid chloride, acid anhydride, thioester, ester, amide.
Hydrolysis
Water to carboxylic acid
Alcoholysis
alcohol to ester
Aminolysis
ammonia or ari amine to amide
Reduction
Reaction with hydride reducing agent to aldehyde or alcohol
Grignard Reaction
Reaction with an organometallic reagent to a ketone or an alcohol
+ SO2 + HCl
What are the most common carboxylic acid derivatives in the lab?
acid halides, acid anyhydrides, esters, and amides
What are the most common carboxylic acid derivatives in biological molecules?
thioesters and acyl phosphates
What reaction dominates carboxylic acid derivatives?
nucleophilic acyl substitution
What are examples of step-growth polymers?
polyamides and polyesters
How are polyamides formed?
Reaction between a diacid and a diamine
How are polyesters formed?
Reaction between a diacid and a diol.
Author
lukemlj
ID
75603
Card Set
Ochem-CH21-COOHs
Description
Ochem-CH21- carboxylic acid derivatives
Updated
2011-04-25T11:18:03Z
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