Chem 2B Ch. 06 Carboxylic Acids

Front 1

A compound that has a cabonyl group bonded to a hydroxyl group, (RCOOH).

Back 1

Carboxylic acid

Front 2

A compound that has a carbonyl group bonded to an -OR' group, (RCOOR').

Back 2

Ester

Front 3

A compound that has a carbonyl group bonded to a nitrogen atom group, RCONR'₂, where the R' groups may be alkyl groups or hydrogen atoms.

Back 3

Amide

Front 4

A reaction in which a new group replaces (substitutes for) a group attached to a carbonyl-group carbon.

Back 4

Carbonyl-group substitution reaction

Front 5

An RC=O group.

Back 5

Acyl group

Front 6

The -COOH functional group.

Back 6

Carboxyl group

Front 7

This group is?

Back 7

Acetyl group

Front 8

The anion that results from ionization of a carboxylic acid, RCOO⁻.

Back 8

Carboxylate anion.

Front 9

An ionic compound containing a cation and a carboxylate acid anion.

Back 9

Carboxylic acid salt

Front 10

The reaction between an alcohol and a carboxylic acid to yield an ester plus water.

Back 10

Esterification

Front 11

The reaction of an ester with aqueous hydroxide ion to yield an alcohol and the metal salt of a carboxylic acid.

Back 11

Saponification

Front 12

A compound formed by reaction of an alcohol with phosphoric acid; may be a monester, ROPO₃H₂; a diester, (RO)₂PO₃H; or a triester, (RO)₃PO; also may be a di-or triphosphate.

Back 12

Phosphate ester

Front 13

The -PO₃²⁻ group in organic phosphates.

Back 13

Phosphoryl group

Front 14

Transfer of a phosphoryl group, -PO₃²⁻, between organic molecules.

Back 14

Phosphorylation.

Front 15

In Carboxylic acid derivatives, what is replaced by other groups?

Back 15

the -OH group of the Carboxylic acid.

Front 16

Which have higher B.P.s, carboxylic acids and their derivatives, or comparable alkanes?

Back 16

carboxylic acids and their derivatives, because they are polar. Also, carboxylic acids and amides that have an H atom can H bond.

Front 17

The portion of the carboxylic acid that does not change during a carbonyl-group substitution reaction is known as:

Back 17

an acyl group

Front 18

The most significant property of carboxylic acids is:

Back 18

their behavior as weak acids.

Front 19

When acting as weak acids, carboxylic acids surrender:

Back 19

the H atom of the carboxyl group.

Front 20

Do carboxylic acids H bond with each other?

Back 20

yes

Front 21

Describe the states of carboxylic acids:

Back 21

Those with:
-Up to 4 carbons are water soluble.
-Straight-chain R groups of up to 9 carbons are volatile liquids with strong, unpleasant odors.
-Acids with R-groups larger than 9 carbons are waxy, odorless solids.

Front 22

How are carboxylic acids named?

Back 22

By replacing the -e ending of the alkane name with -oic acid.
If alkyl substituents or other functional groups are present, number the chain starting with the carboxyl end.

Front 23

More so than other families of organic molecules, many carboxylic acids are named:

Back 23

using common names because they were some of the first organic compounds to be isolated.

Front 24

When using common names, the carbon
atoms attached to the carboxyl group (-COOH) are identified by:

Back 24

the Greek letters α, β, γ, δ, ϵ, and so on rather than numbers.

Front 25

The acyl group that remains after a carboxylic acid loses its -OH is named by:
One very important exception is:

Back 25

replacing the -ic ending of the acid name with -oyl. eg.. benzoic acid with the -OH removed is called a benzoyl group.
One very important exception is the acyl group from acetic acid, which is traditionally called an acetyl group.

Front 26

How are dicarboxylic acids named?

Back 26

By keeping the -e on the alkene name and adding the ending -dioic acid.

Front 27

Most dicarboxylic acids are named by:

Back 27

their common names.

Front 28

How are unsaturated carboxylic acids named:

Back 28

By adding -enoic acid to the root name of the alkene. e.g... H₂C=CHCOOH is named propenoic acid.

Front 29

Describe the carbonyl group substitution reaction:

Back 29

The carboxylic acid reacts with H-Z where is loses its -OH group and gains the Z. The -OH reacts with the H to form water.

Front 30

Which have higher boiling points. Carboxylic acids or esters?

Back 30

Esters have lower B.P.s than carboxylic acids because they cannot H bond with each other. They can still H bond with water though.

Front 31

Describe the properties of esters:

Back 31

-colorless
-volatile liquids with pleasant odors
-many contribute to the fragrances of flowers and fruits.

Front 32

How are esters made?

Back 32

Through the reaction between a carboxylic acid and an alcohol.

Front 33

How are esters named?

Back 33

1) They are named using two words.
2) The first word is the alkyl group name of the alcohol used to make the ester.
3) The second word is the parent name of the carboxylic acid used to make the ester, with the -ic acid ending changed to -ate.
eg.. The reaction of acetic acid and ethyl alcohol yields the ester: ethyl acetate.

Front 34

What is the name of an ester formed from ethanol and benzoic acid?

Back 34

ethyl benzoate

Front 35

Which have higher boiling points, carboxylic acids or unsubstituted amides?

Back 35

unsubstituted amides have higher B.P.s because they have two H atoms which can form multiple H bonds.

Front 36

Are amides basic like amines?

Back 36

NO! The positive charge of the carbonyl group attracts the lone pair of the N atom strongly enough to prevent it from acting as a base by accepting an H atom.

Front 37

How are unsubstituted amides named?

Back 37

By replacing the -ic acid or -oic acid ending with -amide.

Front 38

How are substituted amides named?

Back 38

By identifying the subs with N locants and naming the parent as an unsubstituted amide.

Front 39

All unsubstituted amides (except formamide) are in what state?

Back 39

They are all solids.

Front 40

Do carboxylic acids, esters, and amides all undergo carbonyl-substitution reactions?

Back 40

yes

Front 41

Can disubstituted amides and esters H bond with one another?

Back 41

No, they don't have H atoms. They can H bond with water however.

Front 42

Describe the pH of each:
-carboxylic acids
-esters
-amides

Back 42

-carboxylic acids are acidic
-esters and amides are pH neutral

Front 43

Describe the odor of each:
-carboxylic acids
-esters
-amides

Back 43

-carboxylic acids: pungent
-esters: pleasant
-amides: generally odorless