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102 Cards in this Set
- Front
- Back
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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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