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31 Cards in this Set
- Front
- Back
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carboxylic acid derivatives
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acyl halides- replace -OH with -X
anhydrides- replace -OH with -OCOR amides- replace -OH with -NH2 esters- replace -OH with -OR |
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reactivity of carboxylic acid derivatives
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acyl halides > anhydrides > esters > amides
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acyl halide nomenclature
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aka acid or alkonoyl halides
remove "-ic acid" from alkanoic acid and add "-yl halide" |
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synthesis of acyl halides
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most common is acyl chlorides
RCOOH + SOCl2 = RCOCl PCl3, PCl5, or PBr3 also work |
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Nu acyl sub rxns on acyl chloride
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1. hydrolysis
-Nu-water -product-carboxylic acid and HCl 2. ester conversion -Nu-alcohols -product-ester and HCl 3. amide conversion -Nu-amines or ammonia -product- amide and ammonium chloride |
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Friedel-Crafts Acylation
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attach acyl groups to aromatic rings using an acyl chloride and AlCl3
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reduction of acyl halides
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reagent: H2, Pd/BaSO4, quinoline
product: aldehyde |
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anhydride nomenclature
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aka acid anhydride
RCOOCOR substitute "anhydride" for "acid" |
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acetic anhydride
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ethanoic anhydride
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synthesis of anhydrides
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acyl chloride + carboxylate salt
some cyclic anhydrides can be formed by heating carboxylic acids |
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hydrolysis of anhydrides
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Nu-water
product- 2 carboxylic acids |
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anhydride conversion to amide
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Nu- ammonia
product- amide and ammonium salt (made from the side carboxylic acid product) |
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anhydride conversion to ester
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Nu- alcohol
products: ester and carboxylic acid |
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acylation of anhydrides
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Friedel-Crafts acylation
anhydride + aromatic = alkyl aryl ketone and carboxylate anion |
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Amide nomenclature
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RCONR2
replace "-oic acid" with "-amide" any subs on the nitrogen are listed as prefixes, location is N |
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synthesis of amides
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primary or secondary amines with acyl chloride
ammonia with anhydride |
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hydrolysis of amides
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acidic conditions
Nu-water products- carboxylic acid basic conditions Nu-OH product: carboxylates |
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Hofmann Rearrangement of amides
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amides are converted to primary amines
reagent: BrO- products: primary amine, CO2, Br- |
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reduction of amides
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reagent: lithium aluminum hydride
product: amine No C lost. |
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ester nomenclature
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alkyl alkanoate
aryl alkanoate |
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synthesis of esters
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acidic conditions
carboxylic acid + alcohol = ester and water acyl chlorides or anhydrides can also be used phenolic esters need a base catalyst |
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hydrolysis of esters
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acidic conditions
H3O+ + ester = carboxylic acid and alcohol Nu- water basic conditions OH + ester = carboxylic acid and alcohol Nu-OH |
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triacylglycerols
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fats, esters of long-chain carboxylic acids (fatty acids) and glycerol
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saponification
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fats are hydrolyzed under basic conditions to produce soap
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conversion of esters to amides
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Nu- ammonia
product- amide and alcohol |
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transesterification
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transform one ester into another
a different alcohol attacks the carbonyl C, displacing the original alkoxy group |
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Grignard Addition
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Grignard reagents (RMgX)
2 equivalents can be added to an ester to get a tertiary alcohol Nu sub, then Nu addition |
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Claisen condensation of esters
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basic conditions
2 mol ester react to produce a beta-keto ester or acetoacetic ester enolate ion of one ester acts as a Nu and attacks the second ester. analogous to aldol condensation |
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reduction of esters
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reagent: lithium aluminum hydride
product: two different alcohols |
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phosphate esters
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derivative of phosphoric acid, R groups attached to O to make esters
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phospholipids
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glycerol with two fatty acids and one phosphoric acid attached.
found in living systems, main component of cell membranes, part of nucleic acids. part of ATP |
