OChem Synthesis of carboxylic acids

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Last updated 6:59 AM on 9/7/26
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34 Terms

1
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<p>how to go from primary alcohol to carboxylic acid?</p>

how to go from primary alcohol to carboxylic acid?

use a strong oxidizing agent

  1. know Man im not going to drink alcohol first (primary alcohol) before driving the car

  2. do you have 2 cramp my style, i want to drink alcohol first before driving the car

  3. the CrO3wed Has 2 Shut Op 4 real, I drink alcohol 1st before i drive the car


<p>use a strong oxidizing agent</p><ol><li><p>k<strong>no</strong>w <strong>M</strong>a<strong>n </strong>im not going to drink <strong>alcohol first</strong> (primary alcohol) before driving the <strong>car</strong></p></li><li><p>do you <strong>h</strong>ave <strong>2 cr</strong>amp my style, i want to drink <strong>alcohol first</strong> before driving the <strong>car</strong></p></li><li><p>the <strong>CrO</strong><sub>3</sub>wed <strong>H</strong>as <strong>2 </strong> <strong>S</strong>hut <strong>O</strong>p <strong>4 </strong>real, I drink <strong>alcohol 1st </strong>before i drive the <strong>car</strong> </p></li></ol><p></p>
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how to make a carboxylic acid from an alkyl halide?

  1. make Grignard reagent

  2. react with carbon dioxide then do an acidic workup

  • there will be an extra carbon on the chain now from the CO2


<ol><li><p>make Grignard reagent</p></li><li><p>react with carbon dioxide then do an acidic workup </p></li></ol><ul><li><p>there will be an extra carbon on the chain now from the CO<sub>2</sub></p></li></ul><p></p>
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what is the order of least to most reactive? Ester, acid anhydride, acid halide, and amide?

knowt flashcard image
4
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is Na acidic or basic?

sodium is basic= wants to take proton but not electrons

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<p>how to make acid cholrid from carboxylic acid?</p>

how to make acid cholrid from carboxylic acid?

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<p>how to turn carboxylic acid into acid anhydride? </p>

how to turn carboxylic acid into acid anhydride?

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<p>how to turn acid chloride into carboxylic acid?</p>

how to turn acid chloride into carboxylic acid?

  • Hydrolysis

  • acid workup or base then acid workup


<ul><li><p>Hydrolysis</p></li><li><p>acid workup or base then acid workup</p></li></ul><p></p>
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<p>how to turn acid anhydride into carboxylic acid?</p>

how to turn acid anhydride into carboxylic acid?

  • Hydrolysis

  • acid workup or base then acid workup


<ul><li><p>Hydrolysis</p></li><li><p>acid workup or base then acid workup</p></li></ul><p></p>
9
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<p>how to turn acid chloride into an ester? </p>

how to turn acid chloride into an ester?

  • alcohol under acid conditions or basic versionof alcohol with acid workup after


<ul><li><p>alcohol under acid conditions or basic versionof alcohol with acid workup after </p></li></ul><p></p>
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  • alcohol under acid conditions or basic versionof alcohol with acid workup after


<ul><li><p>alcohol under acid conditions or basic versionof alcohol with acid workup after </p></li></ul><p></p>
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amine

<p>amine </p>
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amine

<p>amine </p>
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Hydride reduction

<p>Hydride reduction </p>
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Hydride reduction

<p>Hydride reduction </p>
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  • forms Grignard reagent

  • the X is any halide (Cl, Br, I,…)


<ul><li><p>forms Grignard reagent</p></li><li><p>the X is any halide (Cl, Br, I,…)</p></li></ul><p></p>
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  • forms Grignard reagent

  • the X is any halide (Cl, Br, I,…)


<ul><li><p>forms Grignard reagent</p></li><li><p>the X is any halide (Cl, Br, I,…)</p></li></ul><p></p>
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organocuperate reaction

  • the R group comes from the reagent


<p>organocuperate reaction</p><ul><li><p>the R group comes from the reagent </p></li></ul><p></p>
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organocuperate reaction

  • the R group comes from the reagent


<p>organocuperate reaction</p><ul><li><p>the R group comes from the reagent </p></li></ul><p></p>
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<p>MEMORIZE ME </p>

MEMORIZE ME

MEMORIZE ME

<p>MEMORIZE ME </p>
20
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<p>what does the fischer esterification rxn look like? </p>

what does the fischer esterification rxn look like?

  • use alcohol and acid catalyst


<ul><li><p>use alcohol and acid catalyst </p></li></ul><p></p>
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<p>what is needed for this hydrolysis rxn? </p>

what is needed for this hydrolysis rxn?

  • need water and acidic conditions

  • will reform alcohol


<ul><li><p>need water and acidic conditions</p></li><li><p>will reform alcohol </p></li></ul><p></p>
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<p>what is required for the Saponification rxn? </p>

what is required for the Saponification rxn?

  • need ester in the presence of base to start

  • then acidic workup is used to turn it into carboxylic acid


<ul><li><p>need ester in the presence of base to start</p></li><li><p>then acidic workup is used to turn it into carboxylic acid</p></li></ul><p></p>
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<p>MEMORIZE ME</p>

MEMORIZE ME

MEMORIZE ME

<p>MEMORIZE ME</p>
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this is a Grignard rxn

<p>this is a Grignard rxn </p>
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what can react with Grignard reagent to make tertiary alcohol?

  • acid chlorides

  • acid anhydrides

  • esters


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what 2 things cannot react with Grignard reagent to make tertiary alcohol?

  • carboxylic acids

  • amides

    • these need acid base chemistry


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  • must be done cold

  • water is used to quench or stop the rxn

  • swap OR with H


<ul><li><p>must be done cold</p></li><li><p>water is used to quench or stop the rxn</p></li><li><p>swap OR with H</p></li></ul><p></p>
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  • water is used to quench or stop the rxn


<ul><li><p>water is used to quench or stop the rxn</p></li></ul><p></p>
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  • the final product has 1 less carbon than when it started

    • denoted by yellow dot


<ul><li><p>the final product has 1 less carbon than when it started </p><ul><li><p>denoted by yellow dot </p></li></ul></li></ul><p></p>
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<p>reduction of a nitrile </p>

reduction of a nitrile



<p></p><p></p>
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<p>formation of nitrile is what type of rxn?</p>

formation of nitrile is what type of rxn?

SN2

  • 1st thing is a cyanide ion

  • nitrile is a C to N tripple bond


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<p>Nitrile hydrolysis </p>

Nitrile hydrolysis

  • need final acid strep or it would remain in carboxylate state


<ul><li><p>need final acid strep or it would remain in carboxylate state </p></li></ul><p></p>
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can also be KCN (potassium cyanide)

  • nucleophilic cyanide ion

This is a nucleophilic addition rxn

  • this rxn will add an extra carbon onto the chain


<p>can also be KCN (potassium cyanide) </p><ul><li><p>nucleophilic cyanide ion </p></li></ul><p><strong>This is a nucleophilic addition rxn </strong></p><ul><li><p>this rxn will add an extra carbon onto the chain </p></li></ul><p></p>
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<p>MEMORIZE ME! </p>

MEMORIZE ME!

MEMORIZE ME!

  • missing cyanohydrin rxn


<p>MEMORIZE ME! </p><ul><li><p>missing cyanohydrin rxn</p></li></ul><p></p>