ch 8 - Carboxylic Acids

Question 1

carboxylic acids

Answer 1

contain both carbonyl and hydroxyl group bonded to the same carbon; always terminal

Question 2

naming carboxylic acids

Answer 2

when priority group, add -oic acid to parent chain and the carbon it is attached to becomes carbon 1.
when in a chain: list the cycloalkane and add “carboxylic acid” at the end. Salts of carboxylic acids are named with the cation followed by -oate; molecules with a carboxylic group on each end are named by adding suffix -dioic acid

Question 3

dimers

Answer 3

pairs of molecules connected by two hydrogen bonds

Question 4

beta-dicarboxylic acids

Answer 4

dicarboxylic acids in which each carboxylic acid is positioned on the beta-carbon of the other (two carboxylic acids separated by a single carbon)

Question 5

synthesis of primary alcohol to carboxylic acid

Answer 5

use KMnO4 (secondary and tertiary ETOh cannot be synthesized to carboxylic acids)

Question 6

Nucleophilic Acyl Substitution

Answer 6

similar to nucleophilic addition to an aldehyde or ketone except for the presence of a leaving group in this reaction; nucleophile opens up to the carbonyl, forms a tetrahedral intermediate, and then the carbonyl reforms, kicking off the leaving group; nucleophilic molecule replaces the leaving group of an acyl derivative

Question 7

acyl derivatives

Answer 7

all molecules with a carboxylic acid-derived carbonyl, including carboxylic acids, amides, esters, anhydrides and others.

Question 8

acyl derivatives focused on by the mcat

Answer 8

carboxylic acids, amides, esters, anhydrides

Question 9

Amide

Answer 9

R-double bond O-C-N-R’

Question 10

formation of amide from carboxylic acid

Answer 10

driven by ammonia (NH3) or an amine (NH2-R)

Question 11

naming amides

Answer 11

named by replacing the -oic acid suffix of carboxylic acid with -amide; any alkyl groups on the nitrogen are placed at the beginning of the name with the prefix N-. Has resonance with the double bond changing from the O-C to C-N bond.

Question 12

lactams

Answer 12

cyclic amides named by replacing the -oic acid of the parent carboxylic acid with -lactam; also named by indicating the specific carbon that is bonded during cyclization of the compound

Question 13

esters

Answer 13

hybrid between a carboxylic acid and an ether (ROR’), can be made by reacting carboxylic acids with alcohols under acidic conditions

Question 14

Esterification

Answer 14

condensation reaction with water a side product; occurs most rapidly with primary alcohols

Question 15

naming esters

Answer 15

name alkane chain beside oxygen (ex ethyl) and then add -oate as suffix to parent alkane on other side with carboxyl

Question 16

lactones

Answer 16

esters that are cyclic; named by replacing -oic acid with -lactone

Question 17

anhydride form

Answer 17

ex. R-C(double bond)O and O connected to C(double bond) O and R’

Question 18

anhydride

Answer 18

formed by the condensation of two carboxylic acids; named by replacing the acid at the end of the name of the parent carboxylic acid with anhydride; same with cyclic; occurs via nucleophilic acyl substitution

Question 19

Reduction of carboxylic acids to primary alcohol

Answer 19

reduced by LiAlH4, sometimes with aldehyde as an intermediate; occurs by nucleophilic addition of hydride to the carbonyl group

Question 20

decarboxylation

Answer 20

complete loss of carboxyl group as CO2

Question 21

saponification

Answer 21

process by which a long-chain carboxylic acid reacts with sodium or potassium hydroxide and forms a salt; occurs by mixing fatty acids with lye (sodium or potassium hydroxide), resulting in formation of salt known as soap

Question 22

soaps

Answer 22

can solvate nonpolar organic compounds in aqueous solutions because they contain both a nonpolar tail and a polar carboxylate head