Chapter 21 Key Words

Front 1

Carboxylic Acid Derivatives

Back 1

Compounds in which an acyl group is binded to an electronegative atom or substituent that can act as a leaving group in a substitution reaction.

Acid halides, acid anhydrides, esters, and amides.

Front 2

Acid Halides

Naming: First, identify the _________ and then the _______.

Back 2

RCOX

acyl group; halide

Front 3

Acid Anhydrides

Naming:
*Symmetrical: Replace the word _________ with ________.
*Unsymmetrical: Name 2 ________ alphabetically and add _____________.

Back 3

RCO2COR'

acid; anhydride

acids; anhydride

Front 4

Amides

Naming: Replace the _______ or ________ with _________.

Back 4

RCONH2

-oic acid; -ic acid; -amide

Front 5

Acyl Phosphates

Naming: Cite the ______ group and add the word __________.

Back 5

RCO2PO3^2- and RCO2PO3R'

acyl; phosphate

Front 6

Esters

Naming: First, identify the ___________ attached to the oxygen and then identify the carboxylic acid by replacing the __________ with __________.

Back 6

RCO2R'

alkyl group; -ic acid; -ate

Front 7

Thioester

Naming:
*Related ester has common name:
*Systematic name: _________ or ___________ is replaced by ________ or ___________.

Back 7

ROCOSR'

*thio-
*-oate; -carboxylate; -thioate; -carbothioate

Front 8

Nucleophilic Acyl Substitution Reaction

Back 8

A reaction in which a nucleophile attacks a carbonyl compound and substitutes for a leaving group bonded to the carbonyl compound.

Front 9

Sterically, unhindered carbonyl groups react with nucleophiles _________ readily than do sterically hindered groups.

Back 9

MORE

Front 10

Electronically, strongly polarized acyl compounds react ________ readily than less polar ones.

Back 10

MORE

Front 11

Hydrolysis

Back 11

Reaction with water to yield a carboxylic acid.

Front 12

Alcoholysis

Back 12

Reaction with alcohol to yield an ester.

Front 13

Aminolysis

Back 13

Reaction with ammonia or an amine to yield an amide.

Front 14

Reduction

Back 14

Reaction with a hydride reducing agent to yield an aldehyde or an alcohol.

Front 15

Grignard Reaction

Back 15

Reaction with an organometallic reagent to yield a ketone or an alcohol.

Front 16

Fischer Esterification Reaction

Back 16

The acid-catalyzed nucleophilic acyl substitution reaction of a carboxylic acid with an alcohol to yield an ester.

Front 17

Acid chlorides react with water to yield ____________.

Back 17

carboxylic acids

Front 18

Nucleophilic acyl substitution reaction of an acid chloride with a carboxylic anion gives an _______________________.

Back 18

acid anhydride

Front 19

Acid chlorides react with alcohols to yield ___________.

Back 19

esters

Front 20

Acid chlorides react rapidly with ammonia and amines to yield _______________.

Back 20

amides

Front 21

Acid chlorides are reduced by LiAlH4 to yield __________.

Back 21

primary alcohols

Front 22

Grignard reagents react with acid chlorides to yield _____________.

Back 22

tertiary alcohols

Front 23

Acid anhydride reacts with alcohols to yield _____________.

Back 23

acetate esters

Front 24

Acetic anhydride reacts with amines to yield ____________.

Back 24

N-substituted acetamides

Front 25

Esters react with aqueous base or acid to yield ______________.

Back 25

carboxylic acid plus alcohol

Front 26

Esters react with ammonia and amines to yield ______________.

Back 26

amides

Front 27

Esters react with LiAlH4 to yield ______________.

Back 27

primary alcohols

Front 28

Esters and lactones react with 2 equivalents of Grignard's reagent to yield ______________.

Back 28

tertiary alcohol

Front 29

Amides react with aqueous acid or base with heat to yield ______________.

Back 29

carboxylic acids plus ammonia OR an amine

Front 30

Amides react with LiAlH4 to yield ______________.

Back 30

amine

Front 31

Stepgrowth Polymers

Back 31

Each bond in the polymer is formed independently of each other.

Front 32

Polyamides are also known as ______________.

Back 32

nylons