Carboxylic Acids Derivatives - Chp 21

Question 1

How to name acyl halides?

Answer 1

Replacing -ane with -yl
ex. ethanoyl fluoride

Question 2

How to name anhydrides?

Answer 2

add “anhydride” to the end
ex. C4H6O3 is acetic anhydride

Question 3

Esters are named as alkyl carboxylates. How do you name them?

Answer 3

Add -oate
ex. phenyl benzoate

Question 4

Cyclic esters are called _______ and named by adding ________.

Answer 4

lactones; acid lactone
ex. 5-hydroxypentanoic acid lactone

Question 5

How to name amides?

Answer 5

Replace -ic or -oic with -amide.
ex. N-ethylethanamide

Question 6

Cyclic amides are called _____. How to name them?

Answer 6

Lactams; Add “acid lactam”
ex. 4-aminobutanoic acid lactam

Question 7

How to name nitriles?

Answer 7

Add -nitrile to the alkane name.
ex. ethanenitrile

Question 8

What determines the parent name of a compound?

Answer 8

The functional group with the highest priority.

Question 9

List the order to priority for the given groups:
Acid
Nitrile
Amide
Aldehyde
Ketone
Alkene
Alkane
Amine
alcohol
Ester
ether
carboxylic acid

Answer 9

carboxylic acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > alkene, alkyne > ether

Question 10

You add ___ for carboxylic acids, ____ for esters, ____ for aldehydes, ___ for ketones, ___ for alcohols, ______ for amides and ______ for nitriles.

Answer 10

-oic acid; -oate; -al; -one; -ol; -amide; -nitrile

Question 11

Do amides have very high b.ps & m.ps compared to other compounds of similar weight?
Melting points _______ with increasing # of _____ bonds.

Answer 11

Yes; increase; N-H

Question 12

List the order of reactivity from most to least with the following functional groups: ester, carboxylate, amide, anhydride, acid chloride

Answer 12

Acid chloride, anhydride, ester, amide, carboxylate

Question 13

List the order of increasing basicity with the following leaving groups: OR, NH2, Cl, COOR,

Answer 13

Cl, COOR, OR, NH2

Question 14

Will a reaction occur if the product is more reactive than the reactants?

Answer 14

No.

Question 15

Carboxylic acid –> acid chloride

Answer 15

SOCl2 or COCl2

Question 16

Anhydride means without water. So removing 1 mole. of water from 2 mole.s of carboxylic acids forms _______.

Answer 16

an anhydride

Question 17

An acid chloride + an acid forms ___________. What attacks what?

Answer 17

an anhydride; OH from acid attacks the carbonyl on acid chloride.

Question 18

Acid + alcohol forms ______. What attacks what?

Answer 18

ester; Alcohol attacks carbonyl.

Question 19

Anhydride + alcohol forms _______. What attacks what?

Answer 19

ester and acid (COOH); Alcohol attacks carbonyl of anhydride

Question 20

Acid chloride + _________ forms an amide.

Answer 20

2 amines (NHR2)

Question 21

Anhydride + amine forms ______.

Answer 21

amide

Question 22

Ester + ______ forms amide.

Answer 22

primary amine or NH3

Question 23

Nitrile + H2O (or H+ or -OH) forms ______, then + H2O and H+ forms ______.

Answer 23

Primary amide; carboxylic acid

Question 24

Carboxylic acid + NH3 and heat forms _____, then + POCl3 forms _______.

Answer 24

primary amide; nitrile

Question 25

Acid chloride + H2O forms _______.

Answer 25

carboxylic acid

Question 26

Amide + H3O forms _____. (Acid hydrolysis)

Answer 26

an acid

Question 27

Ester + LiAlH4 forms ________, then + H3O+ forms ________.

Answer 27

a primary alkoxide; primary alcohol

Question 28

Acyl chlorides + LiAlH(O-t-Bu)3 forms _______.

Answer 28

an aldehyde

Question 29

Ester reacting with 1) DIBAL [(i-Bu)2AlH] 2) H2O forms _______.

Answer 29

an aldehyde

Question 30

What reduces an amides to an amine? (Primary, secondar and tertiary) What attacks what?

Answer 30

1) LiAlH4 2) H2O (Same for all three); H from AlH4 attacks carbonyl

Question 31

Nitrile to primary amine needs what reagent?

Answer 31

H2/Pt or 1) LiAlH4 2) H2O

Question 32

Ester + 2C4H9Li and H3O+ forms _______.

Answer 32

secondary alcohol

Question 33

Acid chloride + 2Grignard and H3O+ forms _______.

Answer 33

a tertiary alcohol

Question 34

Ester + Grignard reagent forms _______, then + Grignard reagent forms ______.

Answer 34

a ketone; an alcohol

Question 35

Nitrile + Grignard and H3O+ forms _______.

Answer 35

a ketone

Question 36

List in increasing order for boiling point for the following groups: ester, amide, alkane, nitrile, acid and alcohol

Answer 36

alkane, ester, nitrile, alcohol, acid, amide

Question 37

Acid chloride + amine (NH2) forms ______.

Answer 37

an amide

Question 38

Acid chloride + an alcohol forms ______.

Answer 38

an ester

Question 39

Amide + 1) LiAlH4 2) H2O forms ______.

Answer 39

an amine (takes out the carbonyl C=O)

Question 40

Ester + NaOH (saponification) forms _______.

Answer 40

carboxylate and an alcohol

Question 41

Nitrile + NaOH (or -OH) and H2O forms _________, twice (again) forms ______.

Answer 41

a primary amide; carboxylate ion and NH3

Question 42

Ester + 2 R''MgX and H2O forms ____________.

Answer 42

A tertiary alcohol.