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Chapter 20
Carboxylic Acid Derivatives
25
Organic Chemistry
Undergraduate 2
03/29/2015

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Term
The greater the resonance, the _____ the C-L bond (shorter or longer?)
Definition
shorter
Term
Which is the least reactive of the carboxylic acid derivatives?
Definition
amide
Term
What is the general formula of an acyl halide?
Definition
RCOX (C and O are double bonded carbonyl group)
Term
carbonyl halides
Definition
the halides of alkane carboxylic acids
Term
The reactions of carboxylic anhydrides with nucleophiles, although less vigorous, are completely analogous to those of the _____
Definition
acyl halides
Term
alkoxycarbonyl
Definition
the ester grouping as a substituent; COOR
Term
lactone
Definition
a cyclic ester
Term
Esters undergo nucleophilic substitution reactions by means of _____ pathways, albeit with reduced reactivity relative to halides & anhydrides
Definition
addition-elimination
Term
2 step mechanism of base-mediated ester hydrolysis
Definition
1. addition-elimination
2. deprotonation
Term
Ester hydrolysis in base requires the loss of a _____
Definition
poor leaving group
Term
Are strong bases poor leaving groups?
Definition
yes!
Term
transesterification
Definition
the acid- or base-catalyzed transformation reaction of esters with alcohols
Term
Lactones are opened to hydroxy esters by _____
Definition
transesterification
Term
How many equivalents of a Grignard reagent are required to convert an ester into an alcohol?
Definition
two
Term
_____ are formed by treatment of esters with strong base as low temperatures due to the high acidity of alpha-hydrogens in esters.
Definition
ester enolates
Term
alkanamides
Definition
another name for amides; the ending "-e" of the alkane stem has been replaced by "-amide"
Term
In common names of amides, the ending "-ic" of the acid name is replaced by the "_____" suffix
Definition
"-amide"
Term
In cyclic amides, the ending "-carboxylic acid" is replaced by "_____"
Definition
"-carboxamide"
Term
lactams
Definition
cyclic amides
Term
Which are the least reactive of the carboxylic acid derivatives?
Definition
the amides
Term
The reactions of amides with LAH produces _____
Definition
amines
Term
alkanitriles
Definition
the IUPAC way of naming nitriles:
(RC(triple bond)N)
Term
In common names of nitriles, the ending "-ic acid" of the carboxylic acid is usually replaced with "_____"
Definition
"-nitrile"
Term
cyano
Definition
the substituent CN
Term
Cyanocycloalkanes are called _____
Definition
cycloalkanecarbonitriles
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