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The flashcards below were created by user
lukemlj
on FreezingBlue Flashcards.
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Nucleophilic Acyl Substitution Reaction
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Nomenclature
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An Sn2 reaction occurs in how many steps? A nucleophilic acyl substitution occurs in how many steps?
One. Two.
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Describe the mechanism for an Sn2 reaction.
Describe the mechanism for a nucleophilic acyl substitution.
- Backside displacement of the leaving group.
- Tetrahedral intermediate.
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In a nucleophilic acyl substitution reaction, ___ carbonyl groups are more reactive.
unhindered
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In a nucleophilic acyl substitution reaction, ___ acyl compounds are more reactive.
strongly polarized
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List the order of reactivty for acid chlorides, amides, esters, thioesters, and acid anhydrides.
Acid chloride, acid anhydride, thioester, ester, amide.
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Hydrolysis
Water to carboxylic acid
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Alcoholysis
alcohol to ester
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Aminolysis
ammonia or ari amine to amide
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Reduction
Reaction with hydride reducing agent to aldehyde or alcohol
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Grignard Reaction
Reaction with an organometallic reagent to a ketone or an alcohol
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 + SO2 + HCl
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What are the most common carboxylic acid derivatives in the lab?
acid halides, acid anyhydrides, esters, and amides
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What are the most common carboxylic acid derivatives in biological molecules?
thioesters and acyl phosphates
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What reaction dominates carboxylic acid derivatives?
nucleophilic acyl substitution
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What are examples of step-growth polymers?
polyamides and polyesters
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How are polyamides formed?
Reaction between a diacid and a diamine
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How are polyesters formed?
Reaction between a diacid and a diol.
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