Ch 20: Carboxylic acids and they are derivatives: NAS Rxn

Question 1

Compounds with parallel properties to carboxylic acids…

Answer 1

R-C triple bond N:

Question 2

The week base who’s conjugate acid has the highest PKA is the ___________. 

Answer 2

Strongest

Question 3

How do you name acyclic acid chlorides by IUPAC?

• acid chlorides come from carboxylic acids

Answer 3

-end in -oyl chloride

Ex:ethanoyl chloride

Question 4

How do you name acid chloride that are in a ring compound by IUPAC? 

Answer 4

Cycloalkane name + carbonyl chloride

Question 5

How do you commonly name acid chlorides?

Answer 5

Prefix + -yl chloride

Question 6

Acid anhydrates derive from…..

Answer 6

Two carboxylic acids

Question 7

How do you name Symmetrical acid anhydrides?

Answer 7

Prefix + -ic anhydride

Question 8

How do you name mix anhydrides?

Answer 8

-two Prefixes + anhydride (alphabetically) 

Question 9

Esters are made of an _____ and an _____ group.

Answer 9

Acyl, alkyl

Question 10

What is the IUPAC and common naming for esters?

Answer 10

IUPAC—— -oate

Common —— -ate

Question 11

How do you name special ring compounds that include Esther‘s?

Answer 11

Name R’ + name of cycloalkane ring + carboxylate

Question 12

How do you name primary acyclic Amides by IUPAC?

Answer 12

• amide

-  names end in amide or Carboxamide 

Question 13

How do you name cyclic primary amides by IUPAC?

Answer 13

Cycloalkane name + carboxamide

Question 14

how do you name amides by the common name?

Answer 14

Prefix + -amide

Question 15

How do you name secondary and tertiary amides by the common name? 

Answer 15

N- prefix before each R’ group

Question 16

How do you name nitriles by IUPAC?

Answer 16

Name ends in -nitrile

-named as alkanenitriles

Question 17

How do you name nitriles by their common name?

Answer 17

-onitrile

Question 18

-CN as a substituent is an ________ group 

Answer 18

Cyano

Question 19

Esters and amides have a higher priority than… 

Answer 19

Nitriles, alcohols, ketones

Question 20

Primary and secondary amides have ______ bonds Between their molecules

Answer 20

Hydrogen

Question 21

L what kind of intermolecular forces do acid chlorides, esters, amides, acid anhydrides, and nitriles have?

Answer 21

Dipole dipole interactions and van der Waals forces

Primary and secondary amides have hydrogen bonding as well 

• have higher BP and MP of comparable nonpolar substances of similar molar mass, primary and secondary amides even higher. 

Question 22

Conjugated carbonyl groups absorb at ________ Frequencies

Answer 22

Lower

Question 23

As carbonyl ring size decreases, carbonyl groups absorb at _________ frequencies

Answer 23

Higher

Question 24

Peptides, polypeptide, proteins are _____ 

Answer 24

Amides

Question 25

What is used to synthesize aspirin?

Answer 25

Acetic anhydride

Question 26

What is a carboxylate?

Answer 26

Conjugate base of carboxylic acid

Question 27

Since Cl is The best leaving group among these compounds, ____________ Are difficult to prepare through acyl nucleophilic substitution reaction

Answer 27

Acid chlorides 

Question 28

What is added to remove the HCl formed with an acid chloride reaction?

Answer 28

Pyridine (neutralizes) 

Question 29

Reactions with acid chloride and carboxylate ions produce

Answer 29

Acid anhydride

Question 30

Reaction with acid chloride and water produces….

Answer 30

A carboxylic acid

Question 31

Acid anhydrides are _______ reactive than acid chloride

Answer 31

Less

Question 32

Reaction of acid anhydride With water produces….

Answer 32

Two carboxylic acids

Question 33

Reaction with acid anhydride with alcohols produce…

Answer 33

An Ester and a carboxylic acid

Question 34

Acid-base reactions are _______ Than nucleophilic ones

Answer 34

Faster

Question 35

What is required in the conversion of dicarboxylic acids to cyclic anhydrides? 

Answer 35

High Heat

Question 36

What reagent is used in Fisher esterfication?  | Carboxylic acid to an ester

Answer 36

H2SO4

Question 37

What reagent is used for intramolecular cyclization of Gamma and Delta hydroxy carboxylic acids? 

Answer 37

H2SO4 Produces gamma-lactone and H2O

Question 38

What is DCC?

Answer 38

A drying agent

Question 39

What reagent is used to convert carboxylic acids to primary amides? 

Answer 39

1. NH3 | 2. heat

Question 40

Esters undergo what three types of reactions?

Answer 40

- hydrolysis in acid - hydrolysis in base - Reactions with amines

Question 41

What reagent is used for ester hydrolysis in acid? What does it produce?

Answer 41

H2SO4  carboxylic acid and alcohol Because it is reversible, a large excess of water is used to drive the reaction to the right

Question 42

What reagent is used for Ester hydrosis in base? What does it produce?

Answer 42

OH- H2O Carboxylate ion and an alcohol

Question 43

Carboxylate ion can be converted to a carboxylic acid with a.….

Answer 43

Strong acid

Question 44

-NH2 is a poor leaving group therefore, ________ Are least reactive OK sometimes covered in the unit. However, they do hydrolyze under strenuous conditions in acid or base

Answer 44

Amides

Question 45

What reagent is used for hydrolysis of amides in acid? What is produce?

Answer 45

H2O H+ Carboxylic acid and an ammonium ion

Question 46

What is produced in hydrolysis of amides in base? | What is the reagent?

Answer 46

A carboxylate ion and an amine H2O OH-

Question 47

The lack of reactivity of ________ amides make Proteins very stable in the body

Answer 47

Amides

Question 48

Nitros do not have leaving groups therefore they do not undergo what type of reactions? What reacting do they go?

Answer 48

Nucleophilic substitution reaction Nucleophilic addition reactions at the electrophilic carbon

Question 49

What reagent is needed for the reduction of nitriles?

Answer 49

Strong reducing agent 1. LiAlH4 2. H2O Reduces to an amine?

Question 50

Reduction of nitriles with 1.DIBAL-H 2.H20 Produces an….

Answer 50

Aldehyde

Question 51

What reagent is used to produce a ketone from nitriles?

Answer 51

1. R’M | 2. H2O