ch 9 - Carboxylic acid derivatives

Question 1

amide general formula

Answer 1

RCONR

Question 2

esterifying group of esters

Answer 2

substituent bonded to the oxygen

Question 3

formation of esters

Answer 3

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

Question 4

triacylglycerols

Answer 4

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

Question 5

anhydrides

Answer 5

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

Question 6

anhydrides to recognize as cyclic

Answer 6

phthalic anhydride and succinic anhydride

Question 7

important carboxylic acid order of reactivity

Answer 7

from most to least: Anhydrides>esters>amides

Question 8

order of electrophilicity of carboxylic acids

Answer 8

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

Question 9

steric hindrance

Answer 9

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

Question 10

induction

Answer 10

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

Question 11

conjugation

Answer 11

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

Question 12

enones

Answer 12

alpha, beta unsaturated carbonyls

Question 13

sp3 angle

Answer 13

109.5 degrees

Question 14

cleavage reaction

Answer 14

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

Question 15

reaction of ammonia and anhydride produces what to eventual products?

Answer 15

amide and carboxylic acid

Question 16

reaction of alcohol and anhydride produces what two products?

Answer 16

ester and carboxylic acid

Question 17

symmetric anhydride + water

Answer 17

carboxylic acid

Question 18

transesterification

Answer 18

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

Question 19

process of hydrolysis of amides

Answer 19

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