Ch. 17-18 info

Question 1

Values of pKa for aliphatic carboxylic acids are in the range

Answer 1

4-5

Question 2

Treating a Grignard reagent with carbon dioxide (CO2) gives the magnesium salt of a carboxylic acid, which, upon protonation with aqueous acid, gives a

Answer 2

carboxylic acid

Question 3

besides lialh4, other reducing agents such as catalytic hydrogenation and NaBH4 cannot reduce a …, so these can be used to reduce other functional groups without affecting a ….group in the same molecule.

Answer 3

carboxylic acid; carboxyl

Question 4

…is used to form methyl esters from carboxylic acids. The mechanism involves protonation of the …by the carboxylic acid to make a methyldiazonium cation, followed by attack of the resulting carboxylate on the methyldiazonium cation to give the ….

Answer 4

diazomethane; diazomethane carbon atom; methyl ester and N2.

Question 5

Carboxylic acids with a carbonyl b to the carboxyl group undergo … upon heating

Answer 5

decarboxylation (loss of CO2)

Question 6

b-Ketoacids decarboxylate upon heating. The mechanism involves redistribution of electrons in a six- membered transition state to give CO2 and the enol of a ketone, which tautomerizes to give a …. The reaction is facilitated by a hydrogen bond between the carboxyl hydrogen atom and b-carbonyl oxygen.

Answer 6

ketone

Question 7

(common names) methanoic acid

Answer 7

formic acid

Question 8

(common names) ethanoic acid

Answer 8

acetic acid

Question 9

(common names) propanoic acid

Answer 9

propionic acid

Question 10

(common names) butanoic acid

Answer 10

butyric acid

Question 11

(common names) pentanoic acid

Answer 11

valeric acid

Question 12

(common names) hexanoic acid

Answer 12

caproic acid

Question 13

The name of the anion is derived from the name of the carboxylic acid by dropping the suffix -ic acid and adding the suffix…

Answer 13

-ate

Question 14

The carboxyl group is one of the organic functional groups most resistant to …

Answer 14

reduction

Question 15

an acyl group is

Answer 15

R-C=O

Question 16

acid halides are named by replacing the ic acid of the parent acid with …

Answer 16

-yl halide

Question 17

acid anhydrides are named by replacing the word acid of the parent acid with …

Answer 17

anhydride

Question 18

the alkyl or aryl group bonded to the O atom is named .., followed by the name of the parent acid in which -ic acid is replaced by …

Answer 18

-ate

Question 19

lactones are … in which the acyl C and O atom are part of the ring

Answer 19

cyclic esters

Question 20

if the n atom of an amide has one or two groups attached, the groups are named after the designator …; then -ic acid of the parent acid is replaced by …

Answer 20

N-; -amide

Question 21

lactams are … in which the acyl C and N atom are part of the ring

Answer 21

cyclic amides

Question 22

the amide acyl C atom is less … than that of the other carboxylic acid derivatives

Answer 22

electrophilic

Question 23

the amide N atom is not …

Answer 23

basic

Question 24

nitriles are named by replacing -oic acid of the parent acid with …

Answer 24

-onitrile

Question 25

imides have two … groups attached to the same N atom

Answer 25

acyl groups

Question 26

imides are considerably more acidic than … due to …. of the negative charge of the N-deprotonation anion over both carbonyls

Answer 26

amides; delocalization