DAT orgo - Carboxylic Acids and Acid Derivatives

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Last updated 1:14 AM on 6/18/26
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27 Terms

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relative reactivity carboxylic acid derivatives

ACid chlorides < anhydrides < carboxylic acids(or esters) < amide < Carboxylates

<p>ACid chlorides &lt; anhydrides &lt; carboxylic acids(or esters) &lt; amide &lt; Carboxylates</p>
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What carbonyl leaving groups do not need catalysts

anhydrides and acid chlorides

<p>anhydrides and acid chlorides </p>
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What carbonyl leaving groups need catalysts

carboxilic acids, esters, amides, and esters

<p>carboxilic acids, esters, amides, and esters </p>
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Nucleophilic acyl addition

knowt flashcard image
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Thionyl chloride

SoCl2

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What determines boiling point in alcohols

the size of the R group

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what makes carboxylic acids have higher boiling points than their alcohol counterparts

dimerization an H bonding

<p>dimerization an H bonding </p>
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How to form a carboxylic acid

use a grignard and a carboxylic acid

followed by a quench

<p>use a grignard and a carboxylic acid</p><p></p><p>followed by a quench </p>
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term image
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Fischer esterification

carboxylic acid into Ester

+ H+ and HOR

<p>carboxylic acid into Ester</p><p></p><p>+ H+ and HOR</p>
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Saponification in acidic conditions

Taking an ester and converting it into a carboxylic acid

+ H+ and water

<p>Taking an ester and converting it into a carboxylic acid </p><p>+ H+ and water </p><p></p>
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Saponification in basic conditions

made in soaps!

<p>made in soaps!</p>
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What does adding NABH4 do

It reduces aldehydes and ketones down into primary and secondary alcohols, respectivley

<p>It reduces aldehydes and ketones down into primary and secondary alcohols, respectivley </p>
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Besides ketones and aldehydes, what else can NaBh4 react with

Anhydrides and acid chlorides

<p>Anhydrides and acid chlorides </p>
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What can LiAlH react with

all carboxylic acid derviartives

<p>all carboxylic acid derviartives </p>
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What happens when your react LiAlH3 with an amide

The reaction anctually forms a primary amide

<p>The reaction anctually forms a primary amide</p>
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Hoffman reaction

it reduces an amide to an amine, but it removes the C=O carbon

Br2 and NaOH

<p>it reduces an amide to an amine, but it removes the C=O carbon </p><p>Br2 and NaOH</p>
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How to do a hydride reduction on an ester that stops at an aldehyde as opposed to a alcohol

DIBAL H at -78 degrees celcius followed by a quench

DIE BALL

<p>DIBAL H at -78 degrees celcius followed by a quench<br><br>DIE BALL</p>
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How to do a hydride reduction on an acid chloride that stops at an aldehyde as opposed to a alcohol

Add LTBA, followed by a quench

<p>Add LTBA, followed by a quench </p>
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Why does DIBAL, and LTBA only reduce esters and acid chlorides down to aldehyde, respectivley

knowt flashcard image
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Adding LiAH3 to nitriles

it forms a primary amine, LAH and N go until it cant

<p>it forms a primary amine, LAH and N go until it cant</p>
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Reacting esters with grignards

Esters plus grignards results in a tertiary alcohol, as grignards do not stop

<p>Esters plus grignards results in a tertiary alcohol, as grignards do not stop </p>
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Reacting acid chlorides with grignards

Much like with esters, it also results in a tertiary alcohol

<p>Much like with esters, it also results in a tertiary alcohol</p>
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Reacting Carboxilic acids with gringnards

Due to the fact that carboxylic acids are acidic, they would react with the R on the grignard to form the deprotenated carboxylate and the R attached to an H

<p>Due to the fact that carboxylic acids are acidic, they would react with the R on the grignard to form the deprotenated carboxylate and the R attached to an H </p>
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Reacting amides with grignard reagents

The Amide is deprotenated once, but nothing else happens

<p>The Amide is deprotenated once, but nothing else happens </p>
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Reacting nitriles with grignards

It forms aa ketone, as initial formation is an immine salt, which then grabs onto H3O to form a ketone

<p>It forms aa ketone, as initial formation is an immine salt, which then grabs onto H3O to form a ketone</p>
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Nitrile hydrolysis

H3o+ and heat

Nitrogen keeps tgrabbing hydrogens until it cant

<p>H3o+ and heat </p><p>Nitrogen keeps tgrabbing hydrogens until it cant</p>