Carboxylic Acids & their derivatives cont

Question 1

When a nucleophile attacks a carbonyl group to form a _______________ the carbonyl group will always be re-formed if possible but H^-(hydride) & C^- (carbanion) are generally not used as leaving groups

Answer 1

Tetrahedral intermediate

Question 2

What are the two core steps in a nucleophilic acyl substitution?

Answer 2

1. Nucleophilic attack
2. Loss of LG

Question 3

In _______ conditions avoid formation of a strong base & in _______ condition such as hydroxide or methoxide avoid formation of a strong acid

Answer 3

Acidic, Basic

Question 4

What is the mechanism pattern for reactions dealing with acid halides?

Answer 4

1. Nucleophilic attack
2. Loss of LG
3. Proton transfer

Question 5

Acid chlorides can be formed by treating carboxylic acids with _________

Answer 5

Thionyl chloride (SOCl₂)

Question 6

When treated with water acid chloride are hydrolyzed to form ___________

Answer 6

Carboxylic acid

Question 7

When treated with alcohol acid chlorides are converted into ___________

Answer 7

Esters

Question 8

When converting acid halides into alcohols can looks from the alcohol point of view and see that the alcohol undergoes ___________

Answer 8

Acylation

Question 9

When two alcohols are present the acyl group attack the ___________ position

Answer 9

less sterically hindered

Question 10

Aminolysis of acid chlorides

Answer 10

When treated with ammonia (NH₃) acid chlorides are converted into amides

Question 11

___________ of acid chlorides has the same mechanism as hydrolysis of an acid chloride

Answer 11

Aminolysis

Question 12

When treated with lithium aluminum hydride (LAH) acid chlorides are reduced to form ___________

Answer 12

Alcohols

Question 13

When acid chlorides are treated with lithium tri(t-butoxy) aluminum hydride (LiAl(OR)₃H) its converted into an ___________

Answer 13

Aldehyde

Question 14

When treated with Grignard reagent acid chlorides are converted in to ___________

Answer 14

Alcohols

Question 15

When acid chlorides are treated with lithium dialkyl cuprate (R₂CuLi)(Gilman reagent) its converted into a ________

Answer 15

Ketone

Question 16

Acetic acids can be converted into __________ with excess heat

Answer 16

Acid anhydrides

Question 17

_________________ can also be formed by treating an acid chloride with a carboxylate ion

Answer 17

Anhydride

Question 18

Reaction for anhydrides are the same as reaction for ______________ (Only difference is the LG for acid chloride is Cl & for anhydride its a carboxylate ion)

Answer 18

Acid chloride

Question 19

____________ are better starting material than acid anhydrides because you only lose a halide & not half of the starting material

Answer 19

Acid halides

Question 20

When treated with a strong base followed by alkyl halide, a carboxylic acid is converted into ___________

Answer 20

Esters

Question 21

Fischer esterification

Answer 21

When carboxylic acids are converted into ester when treated with an alcohol in the presence of an acid catalyst

Question 22

Esters can also be prepared by treating an acid chloride with an ___________

Answer 22

Alcohol (ROH/py)

Question 23

Saponification

Answer 23

Esters being treated with sodium hydroxide followed by an acid to be converted into carboxylic acids (NaOH/H₃O⁺)

Question 24

Esters can also be hydrolyzed under acidic conditions (H₃O⁺) to produce _________

Answer 24

Alcohols

Question 25

Esters can react with amines (NH₃) to produce \_\_\_\_\_\_\_\_\_\_

Answer 25

Amides

Question 26

When esters are treated with LAH they are reduced to form \_\_\_\_\_\_\_\_\_\_

Answer 26

Alcohols

Question 27

Esters can be reduced with DIBAH to make \_\_\_\_\_\_\_\_\_\_\_

Answer 27

Aldehydes

Question 28

When esters are treated with Grignard reagents they are reduced to make ________ with alkyl groups

Answer 28

Alcohols

Question 29

\_\_\_\_\_\_\_\_\_\_ can be produced from any of the carboxylic acid derivatives

Answer 29

Amides

Question 30

Acid chlorides are mostly used to make \_\_\_\_\_\_\_\_\_

Answer 30

Amides

Question 31

When amides are treated with aqueous acid (H₃O⁺) they are reduced to make \_\_\_\_\_\_\_\_\_\_\_\_

Answer 31

Carboxylic acids

Question 32

Amides are hydrolyzed when treated in basic aqueous solution (like NaOH/H₃O⁺) to make \_\_\_\_\_\_\_\_\_\_\_

Answer 32

Carboxylic acid

Question 33

When treated with xs LAH amides are converted into \_\_\_\_\_\_\_\_\_\_

Answer 33

Amines

Question 34

\_\_\_\_\_\_\_\_ can be prepared by treating an alkyl halide with a cyanide ion (NaCN) (SN2 reaction so no tertiary alkyl halide)

Answer 34

Nitriles

Question 35

\_\_\_\_\_\_\_\_\_ can also be made via dehydration of an amide with SOCl₂

Answer 35

Nitriles

Question 36

When treated with aqueous acidic (H₃O⁺) nitriles are hydrolyzed to make ______ which are further hydrolyzed to make \_\_\_\_\_\_\_\_

Answer 36

Amides, Carboxylic acid

Question 37

Nitriles can also be hydrolyzed in aqueous basic condition (NaOH, H₂O) to produce \_\_\_\_\_\_\_\_\_\_\_

Answer 37

Carboxylic acids

Question 38

When nitrile is treated with a Grignard reagent a _______ is formed

Answer 38

Ketone

Question 39

Nitriles are converted in to _______ when treated with LAH

Answer 39

Amines

Question 40

What are the two types of C-C bond-forming reactions?

Answer 40

1. C-C bonds formation where the functional group stayed in the same place 2. C-C bond forming reaction where the functional group position changed

Question 41

What is wavenumber for acid chloride in IR spectrum?

Answer 41

1800

Question 42

What is wavenumber for anhydride in IR spectrum?

Answer 42

1760 & 1820

Question 43

What is wavenumber for carboxylic acid in IR spectrum?

Answer 43

1760

Question 44

What is wavenumber for ester in IR spectrum?

Answer 44

1740

Question 45

What is wavenumber for ketone in IR spectrum?

Answer 45

1720

Question 46

What is wavenumber for amide in IR spectrum?

Answer 46

1660

Question 47

The carbonyl group of a carboxylic acid derivative signal is between __________ in ¹³C spectrum

Answer 47

160-185ppm

Question 48

The carbon atom in a nitrile produces a signal around _________ in ¹³C spectrum

Answer 48

115-130 ppm

Question 49

The proton of a carboxylic acid usually produces a signal around _______ in HNMR

Answer 49

12ppm