Carboxylic Acids and Derivatives

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Chemistry

Organic Chemistry

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<p>carboxylic acids in basic organic environment</p>

carboxylic acids in basic organic environment

deprotonates; resonance; spectator ion

<p>deprotonates; resonance; spectator ion</p>
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<p>carboxylic acids in basic aqueous environment</p>

carboxylic acids in basic aqueous environment

deprotonates; resonance; spectator ion

<p>deprotonates; resonance; spectator ion</p>
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<p>carboxylic acids in acidic organic environment</p>

carboxylic acids in acidic organic environment

Fischer’s esterification; reversible; equilibrium

<p>Fischer’s esterification; reversible; equilibrium</p>
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<p>carboxylic acids in acidic aqueous environment</p>

carboxylic acids in acidic aqueous environment

no change; exchangable protons

<p>no change; exchangable protons</p>
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carboxylic acids in base mechanism

deprotonation

<p>deprotonation</p>
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Fischer’s esterification mechanism

carbonyl oxygen attacks acid → protonation

forms hemiacetal

protonation and dehydration

reform carbonyl via deprotonation

<p>carbonyl oxygen attacks acid → protonation</p><p>forms hemiacetal</p><p>protonation and dehydration</p><p>reform carbonyl via deprotonation</p>
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<p>transesterifcation</p>

transesterifcation

switch R group on ester; essentially Fischer’s esterification mechanism

<p>switch R group on ester; essentially Fischer’s esterification mechanism</p>
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ester

carbonyl + ester; formed from carboxylic acids

<p>carbonyl + ester; formed from carboxylic acids</p>
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<p>ester hydrolysis</p>

ester hydrolysis

reverse of Fischer esterification; reversible

<p>reverse of Fischer esterification; reversible</p>
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<p>ozonolysis and oxidation of an alkene</p>

ozonolysis and oxidation of an alkene

2x carboxylic acid

<p>2x carboxylic acid</p>
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<p>addition of KMnO4 to substituted benzene</p>

addition of KMnO4 to substituted benzene

benzoic acid

<p>benzoic acid</p>
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strong oxidants

HNO3, KMnO4, CrO3, K2Cr2O7, RuO4

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<p>addition of chromate salt to aldehyde</p>

addition of chromate salt to aldehyde

carboxylic acid

<p>carboxylic acid</p>
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<p>Reaction of Organometallic Reagents with Carbon Dioxide</p>

Reaction of Organometallic Reagents with Carbon Dioxide

carboxylic acid

<p>carboxylic acid</p>
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Reaction of Organometallic Reagents with Carbon Dioxide

attack on carbon of CO2

protonation

<p>attack on carbon of CO2</p><p>protonation</p>
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<p>decarboxylation</p>

decarboxylation

removes one acid; needs one carboxylic acid at the beta position of another

<p>removes one acid; needs one carboxylic acid at the beta position of another</p>
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decarboxylation mechanism

proton transfer

enol → keto

<p>proton transfer</p><p>enol → keto</p>
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keto-enol tautomerization

many aldehydes and ketones are in equilibrium with a structural isomer known as the enol form; not resonance forms but structural isomers that can interconvert

<p><span>many aldehydes and ketones are in </span>equilibrium<span> with a structural isomer known as the </span>enol<span> form; </span>not resonance forms but structural isomers that can interconvert</p>
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<p>addition of DCC and amine to carboxylic acid</p>

addition of DCC and amine to carboxylic acid

amide synthesis; reversible; urea side product

<p>amide synthesis; reversible; urea side product</p>
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addition of DCC and amine to carboxylic acid mechanism

carbonyl oxygen attack on carbon

nitrogen deprotonates

amine addition

nitrogen deprotonates

<p>carbonyl oxygen attack on carbon</p><p>nitrogen deprotonates</p><p>amine addition</p><p>nitrogen deprotonates</p>
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<p>addition of sulfurous dichloride to carboxylic acid</p>

addition of sulfurous dichloride to carboxylic acid

acid chloride; reversible with NaOH and acid

<p>acid chloride; reversible with NaOH and acid</p>
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addition of sulfurous dichloride to carboxylic acid mechanism

make carbonyl a good leaving group

make alcohol a carbonyl

<p>make carbonyl a good leaving group</p><p>make alcohol a carbonyl</p>
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<p>addition of organolithium to carboxylic acid</p>

addition of organolithium to carboxylic acid

carbonyl

<p>carbonyl</p>
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addition of organolithium to carboxylic acid mechanism

knowt flashcard image
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<p>addition of lithium aluminium hydride to carboxylic acid</p>

addition of lithium aluminium hydride to carboxylic acid

reduction to primary alcohol; also turns aldehyde into primary alcohol, ketone into secondary alcohol; ester into primary alcohol; amide into amine, nitrile into primary amine

<p>reduction to primary alcohol; also turns aldehyde into primary alcohol, ketone into secondary alcohol; ester into primary alcohol; amide into amine, nitrile into primary amine</p>
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addition of lithium aluminium hydride to carboxylic acid

knowt flashcard image
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<p>addition of sodium borohydride to carboxylic acid</p>

addition of sodium borohydride to carboxylic acid

doesn’t work, only reduces aldehydes and ketones

<p>doesn’t work, only reduces aldehydes and ketones</p>
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<p>addition of nucleophile to acid chloride</p>

addition of nucleophile to acid chloride

SN1 type reaction

<p>SN1 type reaction</p>
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<p>addition of base to acid chloride</p>

addition of base to acid chloride

ester

<p>ester</p>
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<p>addition of hydroxide to acid chloride</p>

addition of hydroxide to acid chloride

carboxylic acid

<p>carboxylic acid</p>
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<p>addition of secondary amine to acid chloride</p>

addition of secondary amine to acid chloride

amide

<p>amide</p>
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<p>addition of benzene and aluminum chloride to acid chloride</p>

addition of benzene and aluminum chloride to acid chloride

Friedel-Crafts acylation

<p>Friedel-Crafts acylation</p>
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<p>addition of organolithium/Grignard reagent to acid chloride</p>

addition of organolithium/Grignard reagent to acid chloride

tertiary alcohol

<p>tertiary alcohol</p>
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addition of organolithium/Grignard reagent to acid chloride mechanism

knowt flashcard image
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<p>addition of organocuprate to acid chloride</p>

addition of organocuprate to acid chloride

ketone; like RLi but more selctive; will not react with ketone/aldehyde

<p>ketone; like RLi but more selctive; will not react with ketone/aldehyde</p>
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<p>addition of lithium aluminium hydride to acid chloride</p>

addition of lithium aluminium hydride to acid chloride

tertiary alcohol

<p>tertiary alcohol</p>
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<p>addition of lithium tri-tert-butoxyaluminum hydride to acid chloride</p>

addition of lithium tri-tert-butoxyaluminum hydride to acid chloride

aldehyde; doesn’t react with aldehydes/ketones

<p>aldehyde; doesn’t react with aldehydes/ketones</p>
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<p>addition of diazomethane to carboxylic acid</p>

addition of diazomethane to carboxylic acid

methyl ester

<p>methyl ester</p>
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<p>addition of aqueous sodium hydroxide to ester</p>

addition of aqueous sodium hydroxide to ester

saponification, deprotonated

<p>saponification, deprotonated</p>
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<p>combination of two carboxylic acids @ 300°C</p>

combination of two carboxylic acids @ 300°C

anhydride and water

<p>anhydride and water</p>
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<p>addition of deprotonated acid to acid chloride</p>

addition of deprotonated acid to acid chloride

anhydride and salt

<p>anhydride and salt</p>
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<p>addition of DIBAL-H to ester @ -78°C</p>

addition of DIBAL-H to ester @ -78°C

aldehyde

<p>aldehyde</p>
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<p>addition of organolithium/Grignard reagent to ester</p>

addition of organolithium/Grignard reagent to ester

tertiary alcohol

<p>tertiary alcohol</p>
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<p>addition of amine to anhydride</p>

addition of amine to anhydride

amide

<p>amide</p>
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addition of amine to anhydride mechanism

knowt flashcard image
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resonance of amide

stability

<p>stability</p>
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<p>amide in basic aqueous environment</p>

amide in basic aqueous environment

deprotonated carboxylic acid and neutral amine; electrophlic attack from carbonyl oxygen

<p>deprotonated carboxylic acid and neutral amine; electrophlic attack from carbonyl oxygen</p>
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<p>amide in acidic aqueous environment</p>

amide in acidic aqueous environment

carboxylic acid and positive amine; nucleophilic attack on carbonyl carbon

<p>carboxylic acid and positive amine; nucleophilic attack on carbonyl carbon</p>
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<p>lithium aluminium hydride reduction on amide</p>

lithium aluminium hydride reduction on amide

amine; could use deuterated reagent

<p>amine; could use deuterated reagent</p>

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