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13 Cards in this Set
- Front
- Back
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Carboxylic Acids: Nomenclature
what happens when it is a salt? |
- suffix is -oic acid
- suffix is -ate |
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Carboxylic Acids: Physical Properties
> A. Hydrogen Bonding > B. Acidity > attributed to? > with adjacent e-withdraw/e-donating groups? |
A. polar, can form hydrogen bonds. can form dimers, which causes HIGH B.P.
B. Due to resonance stabilization of carboxylate anion. > e- withdrawing INCREASE acidity, e- donating DECREASE acidity. |
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Carboxylic Acids: Synthesis
3 types |
- Oxidation Reaction
- Carbonation of Organometallic Reagents - Hydrolysis of Nitriles |
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Synthesis: Oxidation
reagents? |
- aldehydes/primary alcohols/alkylbenzenes + KMnO4
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Synthesis: Carbonation of Organometallic Reagents
first reagents? main reagents? |
- tertiary alkyl halides + Mg/ether = grignard reagent.
-- so (((grignard + CO2/ H+, H2O >>> carboxylic acid))) > basically #C + 1C |
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Synthesis: Hydrolysis of Nitriles
nucleophile? what is target? Product(s)? what type of conditions necessary |
- contain CN- group, a good nucleophile
> will attack primary/secondary halides > Sn2 reaction - can use acidic or basic conditions. - products are C.A. and ammonia. |
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Carboxylic Acids: Reactions
3 types |
- Soap Formation
- Nucleophilic Substitution - Decarboxylation |
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Reactions: Soap Formation
reagents? product? > new ability gained? what happens in aqueous solution? |
- long chain C.A.'s + NaOH or KOH >>> salts
- able to solubilize nonpolar organic compounds in aqueous solution. > they form micelles in aqueous solution |
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Reactions: Nucleophilic Substitutions
3 types |
- Reduction
- Ester Formation - Acyl Halide Formation |
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Nucleophilic Substitutions: Reduction
reagents? product? |
- use LAH to reduce to alcohols.
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Nucleophilic Substitutions: Ester Formation
reagents? conditions? product? which type of nucleophile is most favored for this reaction? |
- alcohols under ACIDIC conditions
- a primary alcohol is most favorable nucleophile |
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Nucleophilic Substitutions: Acyl Halide Formation
reagent(s)? properties of Acyl Halides? what does this do to carbonyl carbon? |
- acyl halides - compounds with carbonyl groups bonded to halides.
- thionyl chloride (SOCl2) + C.A. >>> Acyl halide - VERY HIGH energy, VERY UNSTABLE in the carbonyl family. - makes carbonyl carbon more susceptible to nucleophilic attack. |
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Reactions: Decarboxylation
what type of C.A.'s can undergo this? reagent? |
- loss of CO2
- 1,3-dicarboxylic acids and other Beta-Keto acids - HEAT IS THE REAGENT |
