Exam 2 - Carboxylic Acids

Question 1

In ___, a carboxylic acid can react with 1) NaOH 2) alkyl halide in order to form an ester.

Answer 1

O-Alkylation

Question 2

In Pinnick Oxidation, an aldehyde + ___, ___ will produce a carboxylic acid.

Answer 2

NaClO2, NaH2PO4

Question 3

___ - No double bond to N.

Answer 3

amine

Question 4

A carboxylic acid can react with ___ to make an acid chloride.

Answer 4

SOCl2 (thionyl chloride)

Question 5

In Pinnick Oxidation, an aldehyde + NaClO2, NaH2PO4 will produce a ___ ___.

Answer 5

carboxylic acid

Question 6

In Ozonolysis, an alkene + 1) O3 2) H2O2 will produce ___ ___ ___.

Answer 6

two carboxylic acids

Question 7

*Note, a carboxylic acid can react with ___ to make a primary alcohol.

Answer 7

LiAlH4

Question 8

Amides have a better resonance structure because ___ is ___ ___, so the positive charge on it is okay.

Answer 8

N is less electronegative, so the positive charge on it is okay

Question 9

In the Grignard Reaction with Dry Ice, an alkyl halide can react with 1) Mg 2) CO2(s) 3) H3O+ in order to produce a ___ ___.

Answer 9

carboxylic acid

Question 10

___ and ___ ___ determine carboxylic acid reactivity.

Answer 10

Resonance and LG Ability

Question 11

imine - ___ ___ ___ ___.

Answer 11

imine - Double bond to N

Question 12

Jones’ Oxidation can also be used with an aldehyde in order to produce a ___ ___.

Answer 12

carboxylic acid

Question 13

The better the LG, the more ___ the carboxylic acid.

Answer 13

better the LG = more reactive

Question 14

In Jones’ Oxidation, a primary alcohol + CrO3, H2SO4, and H2O will produce a ___ ___.

Answer 14

carboxylic acid

Question 15

Order of reactivity of carboxylic acid derivatives (from most reactive to least reactive):

Answer 15

acid chlorides > acid anhydrides > aldehydes > ketones > esters = carboxylic acids > amides > carboxylates

Question 16

___ ___ can become all other carboxylic acid derivatives.

Answer 16

acid chlorides

Question 17

Grignard Reaction with Dry Ice will ___ ___ ___.

Answer 17

add 1 carbon (from CO2)

Question 18

The ___ the LG’s conjugate acid pka, the better the LG is.

Answer 18

lower

Question 19

Acid Anhydride has a poor resonance structure due to having ___ ___ ___ near each other.

Answer 19

two positive charges near each other = bad resonance structure

Question 20

In the Grignard Reaction with Dry Ice, an alkyl halide can react with 1) ___ 2) ___ 3) ___ in order to produce a carboxylic acid.

Answer 20

1) Mg 2) CO2(s) 3) H3O+

Question 21

A carboxylic acid can react with diazomethane (CH2N2) to make a ___ ___.

Answer 21

methyl ester

Question 22

*Note, an ylide can not only be stabilized by a nextdoor carbonyl group, an ylide can also be stabilized by ___ ___ ___.

Answer 22

frequent non-carbonyl conjugation

Question 23

In ___ ___, an aldehyde + NaClO2, NaH2PO4 will produce a carboxylic acid.

Answer 23

Pinnick Oxidation

Question 24

___ with a ___ ___ will not lose carbons.

Answer 24

Ozonolysis with a cyclic alkene will not lose carbons

Question 25

Jones’ Oxidation can also be used with a(n) ___ in order to produce a carboxylic acid.

Answer 25

aldehyde

Question 26

A ___ ___ can react with diazomethane (CH2N2) to make a methyl ester.

Answer 26

carboxylic acid

Question 27

*Note, a carboxylic acid can react with LiAlH4 to make a ___ ___.

Answer 27

primary alcohol

Question 28

In Jones’ Oxidation, a ___ ___ and ___, ___, ___ will produce a carboxylic acid.

Answer 28

primary alcohol, CrO3, H2SO4, and H2O

Question 29

O-Alkylation of carboxylic acids to esters only works with ___ ___ ___.

Answer 29

primary alkyl halides

Question 30

Ozonolysis with a straight alkene will ___ ___ ___.

Answer 30

lose 1 carbon

Question 31

In O-Alkylation, a carboxylic acid can react with 1) NaOH 2) alkyl halide in order to form a(n) ___.

Answer 31

ester

Question 32

___ - Double bond next to N.

Answer 32

enamine

Question 33

In the Grignard Reaction with Dry Ice, a(n) ___ ___ can react with 1) Mg 2) CO2(s) 3) H3O+ in order to produce a carboxylic acid.

Answer 33

alkyl halide

Question 34

___ = Deprotonated carboxylic acid.

Answer 34

Carboxylate

Question 35

Ozonolysis with a cyclic alkene will ___ ___ ___.

Answer 35

not lose carbons

Question 36

A ___ ___ can react with SOCl2 to make an acid chloride.

Answer 36

carboxylic acid

Question 37

A carboxylic acid can react with SOCl2 to make a(n) ___ ___.

Answer 37

acid chloride

Question 38

enamine - ___ ___ ___ ___ ___.

Answer 38

enamine - Double bond next to N

Question 39

Aldehydes are ___ ___ than ketones.

Answer 39

more reactive (less stable)

Question 40

You can write “H+ transfer” ONLY in the ___ mechanism.

Answer 40

imine mechanism

Question 41

In ___, an alkene + 1) O3 2) H2O2 will produce two carboxylic acids.

Answer 41

Ozonolysis

Question 42

Carboxylate = ___ ___ ___.

Answer 42

Deprotonated carboxylic acid

Question 43

___ ___ with ___ ___ will add 1 carbon.

Answer 43

Grignard Reaction with Dry Ice will add 1 carbon (from CO2)

Question 44

Acid Chloride’s resonance structure does not have good ___.

Answer 44

Does not have good overlap

Question 45

If a molecule has both an aldehyde and a ketone, then the ___ will get protected first (become a cyclic acetal).

Answer 45

aldehyde

Question 46

In O-Alkylation, a carboxylic acid can react with 1) ___ 2) ___ in order to form an ester.

Answer 46

1) NaOH 2) alkyl halide

Question 47

___ - Double bond to N.

Answer 47

imine

Question 48

___ with a ___ ___ will lose 1 carbon.

Answer 48

Ozonolysis with a straight alkene will lose 1 carbon

Question 49

The better the ___, the more reactive the carboxylic acid.

Answer 49

better the LG = more reactive

Question 50

In ___ ___, a primary alcohol + CrO3, H2SO4, and H2O will produce a carboxylic acid.

Answer 50

Jones’ Oxidation

Question 51

The lower the LG’s conjugate acid pka, the ___ the LG is.

Answer 51

better

Question 52

amine - ___ ___ ___ ___ ___.

Answer 52

amine - No double bond to N

Question 53

In Ozonolysis, an alkene + 1) ___ 2) ___ will produce two carboxylic acids.

Answer 53

1) O3 2) H2O2

Question 54

A carboxylic acid can react with ___ to make a methyl ester.

Answer 54

diazomethane (CH2N2)