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1

amide general formula

RCONR

2

esterifying group of esters

substituent bonded to the oxygen

3

formation of esters

either through Fischer esterification in which mixtures of carboxylic acids and alcohols will condense into esters under acidic conditions; and through reaction of anhydrides and alcohols; have lower boiling points than carboxylic acid they're derived from typically

4

triacylglycerols

storage form of fats in the body; esters of long-chain carboxylic acids (fatty acids) and glycerol (1,2,3-propanetriol)

5

anhydrides

also called acid anhydrides - condensation dimers of carboxylic acids; general formula is RC(O)OC(O)R; often have higher boiling points than their carboxylic acids because of greater weight

6

anhydrides to recognize as cyclic

phthalic anhydride and succinic anhydride

7

important carboxylic acid order of reactivity

from most to least: Anhydrides>esters>amides

8

order of electrophilicity of carboxylic acids

anhydrides (because they have resonance stability and three electron withdrawing oxygen atoms)>esters (which lack one electron withdrawing carbonyl oxygen>amides (with an electron-donating amino group

9

steric hindrance

when a reaction does not proceed due to size of the substituents

10

induction

refers to the distribution of charge across sigma bonds. electrons are attracted to atoms that are more electronegative, creating a dipole across the sigma bond

11

conjugation

refers to presence of alternating single and multiple bonds; implies that all atoms involved in these bonds are either sp2- or sp-hybridized - and therefore have unhybridized p-orbitals

12

enones

alpha, beta unsaturated carbonyls

13

sp3 angle

109.5 degrees

14

cleavage reaction

reaction that splits an anhydride in two; ammonia acts as the nucleophile, one of the carbonyl carbons acts as the electrophile, and a carboxylic acid is the leaving group

15

reaction of ammonia and anhydride produces what to eventual products?

amide and carboxylic acid

16

reaction of alcohol and anhydride produces what two products?

ester and carboxylic acid

17

symmetric anhydride + water

carboxylic acid

18

transesterification

process by which alcohols act as nucleophiles and displace the esterifying group on an ester; in this process one ester is transformed into another

19

process of hydrolysis of amides

under highly acidic conditions they can be hydrolyzed via nucleophilic substitution; acid allows the carbonyl oxygen to become deprotonated making the molecule more susceptible to nucleophilic attack by a water molecule; products are carboxylic acid and ammonia; reverse condensation reaction of the formation of amides. under highly basic conditions hydrolysis occurs the same except carbonyl oxygen is not protonated and nucleophile is a hydroxide ion - product is the deprotonated carboxylate anion