Carboxylic Acids And Derivatives

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What oxidizing aromatic side-chains, what is required?

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A C-H benzylic bond and very strong oxidizing agents:
K2CrO7/H2SO4 or KMnO4

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List some ways to synthesize a carboxylic acid.

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Reducing benzylic side-chains, ozonolysis of alkenes, organometallic addition to CO2, nitrile hydrolysis

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How does organometallic additions to CO2 work?

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When should you use nitrile hydrolysis to make a carboxylic acid and what are the conditions?

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When you have a halide that can be substituted with SN2 for a nitrile group

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How do you protect an alcohol?

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How do EWG and EDG affect acidity of carboxylic acids?

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EWG will increase acidity
EDG will decrease acidity

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What do carboxylates look like, how are they made, and what are they used for?

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They are made by deprotonating the alcohol. They are used for SN2

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How does the reaction between carboxylic acid and diazomethane work?

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Why does the nucleophilic acyl substitution not have an SN2 mechanism?

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x = OH, OR, Cl, SR, NR2, etc
There is too much steric hindrance between R and X

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Mechanism of the neutral nucleophilic acyl substitution?

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How does base catalyzed nucleophilic acyl substitution work?

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The base will protonate the C=O, activating it, and it will also protonate the X, making it a better leaving group.

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What is the most reactive carboxylic acid derivative and which si the least reactive?

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acyl chloride > anhydride > ester > CA > amide > nitrile

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Mechanism for acid catalyzed Fischer esterification?

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Mechanism for acid catalyzed ester hydrolysis?

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Mechanism for base catalyzed ester hydrolysis?

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What are 3 reagents used to turn a CA into an acyl chloride?

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SOCl2, PCl3 and PCl5

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How does SOCl2 turn CA into acid chloride?

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What's a method of forming an ester?

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Acid chloride + alcohol

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When is transesterification ever useful?

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When you have lots of R2OH and it's cheap. It is used in excess

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What is a bad way to make an amide?

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Directly try to put amine and CA together... it will only yield an ammonium salt and a carboxylate
with the exception being formyl derivatives

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What is a good way to make an amide? Draw the overall scheme

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ACYL CHLORIDES + CA = AMIDES :D
socl sokkl sokkul

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What are Schotten-Baumann conditions and what are they used for?

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It is when you have an amine in NaOH/H2O, and slowly add your acid chloride. The result amide will precipitate out of your solution. Can also form an ester out of this.

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Which reducing agents will and will not reduce a CA?

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LiAlH4 and BH3 will reduce CA
NaBH4 and H2/Pd will not reduce CA

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How does DIBAL-H reduce carboxylic acids?

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What are the conditions for DIBAL-H reduction?

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Intermediates?

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When adding to a carboxylic acid, what is the difference between products when using organolithium and Grignard reagents?

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With Grignard, you add the alkyl group twice, and you have an alcohol, but with organolithium, the alkyl group only adds once and the carbonyl stays intact.

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How does organolithium reagent reduce carboxylic acids?

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What is LiAlH(OtBu)3 used for and how is it made?

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It is a reducing agents which is attenuated, and won't reduce aldehydes. You can use it to reduce acyl chlorides to an aldehyde.

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What's so special about organocopper reagents?

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RCuLi - do not reduce ketones - turn acyl chloride into ketone

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NR

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How to make organocopper reagent?

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How are nitrile groups oxidized to aldehydes?

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How are nitrile groups oxidized to ketones?

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Show a map of how R-CN can be utilized.

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How to Weinreb?

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