Brainscape's Knowledge GenomeTM

Browse over 1 million classes created by top students, professors, publishers, and experts.


See full index

Organic Chemistry 2 > Chapter 20-Carboxylic Acids and their Derivatives > Flashcards

Chapter 20-Carboxylic Acids and their Derivatives Flashcards

You may prefer our related Brainscape-certified flashcards:
Periodic Table flashcards Chemistry 101 flashcards AP® Chemistry flashcards Organic Chemistry 101 flashcards
1
Q

Suffix for Carboxylic Acid (IUPAC Nomenclature)

A

“-oic acid”

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
2
Q

What geometry do carboxylic acids have?

A

Trigonal Planar

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
3
Q

Considering carboxylics are soluble in polar solvents…when do they become amphiphilic (hydrophobic)?

A

Amphiphilic when chain is longer than 4 carbons.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
4
Q

What is a carboxylate ion? (Hint: Draw it out!)

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
5
Q

Suffix for Carboxylate ion (IUPAC Nomenclature)

A

“-oate”

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
6
Q

pKa of Carboxylic Acids

A

~4-5

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
7
Q

True or False: Out of ALL of the organic functional groups carboxylic acids are the WEAKEST acids.

A

False, they are still weaker acids, but they are the strongest out of all of the functional groups.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
8
Q

Do electron withdrawing groups (EWG) or electron donating groups (EDG) increase the acidity of Carboxylic Acids?

A

EWGs in crease the acidity.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
9
Q

What are TWO oxidative cleavage routes to make carboxylic acids? (Hint: Think back to Organic Chemistry I!)

A

-KMnO4 w/ H2O and heat
-Ozonolysis (1) O3, 2) H2O)

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
10
Q

Name the TWO conditions in STRONG oxidation that an alcohol group must meet in order to form a carboxylic acid? (Hint: Think back to the first unit or two from this semester!)

A

1) Na2Cr2O7
2) H2SO4, H2O

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
11
Q

Name the two reagents used after forming the grignard reagent in order to form a carboxylic acid?

A

-CO2
-H3O+

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
12
Q

Provide a saponification mechanism for the following reaction.

A
How well did you know this?
1
Not at all
2
3
4
5
Perfectly
13
Q

What reagents can be used to reduce a carboxylic acid to an alcohol?

A

LAH and H3O+

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
14
Q

What is the first thing the carboxylic acid can become in reduction? What is the second thing?

A

1) Aldehyde
2) Alcohol

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
15
Q

What is the othe reactant that can be used in place of LAH in reduction? Why is it a good subsitute for the LAH reagent?

A

BH3 (w/ THF) can be used. BH3 is chemoselctive for the carboxylic acid so therefore it will always react with the acid and will not react with an ester.

How well did you know this?
1
Not at all
2
3
4
5
Perfectly
16
Q

Using Fischer Esterfication. Provide the mechanism for the following reaction.

A
17
Q

What is the poor route of making an amide from a carboxylic acid?

A

Forming an ammonium carboxylate salt than heating it to well above 100 degrees Celcius.

18
Q

What is the better route of synthesizing an amide from a carboxylic acid?

A

The use of an acid chloride.

19
Q

Recall: How do you prepare an acid chloride?

A

Transform a carboxylic acid with SOCl2 to make an acid chloride.

20
Q

Provide the first part of the mechanism of preparing an acid chloride.

A
21
Q

Provide the second part of the mechanism of preparing an acid chloride. What is the mechanism called?

A

Nucleophilic Acyl Substituion

22
Q

What are the five carboxylic acid derivatives?

A

-Acid Halide
-Acid Anhydride
-Ester
-Amide
-Nitrile

23
Q

What is the suffix change from a carboxylic acid (“-ic acid”) to an Acid Halide?

A

“-yl halide”

24
Q

What is the suffix change from a carboxylic acid (“-ic acid”) to an Anhydride?

A

“-Anhydride”

25
Q

What is the suffix change from a carboxylic acid (“-ic acid”) to an Ester?

A

“-ate”

26
Q

What is the suffix change from a carboxylic acid (“-ic acid”) to an Amide?

A

“-amide”

27
Q

What is the suffix change from a carboxylic acid (“-ic acid”) to an Nitrile?

A

“-onitrile”

28
Q

Label the following from a scale 1-4, 1 being the least reactive and 4 being the most reaction:
-Acid Halide
-Ester
-Anhydride
-Amide

A

1-Amide
2-Ester
3-Anhydride
4-Acid Halide

29
Q

Define Nucleophilic Acyl Substitution.

A

The transfer of an acyl group to the attacking nucleophile.

30
Q

Most of the reactions are the same, and because I know you and I, and the whole world would be happier not rewriting this several billion times. Provide the general mechanism for the base conditions of these reactions.

A
31
Q

Howdy! Again, I know you don’t want to rewrite this mechanism a million times. Guess what? Nor do I! Let’s make this easier. Provide the general mechanism for the acid conditions of these reactions.

A
32
Q

Is a base a poor or strong nucleophile? Is an acid a poor or strong nucleophile?

A

A base is always, with a few exceptions, a strong nucleophile. An acid is also, always , with a few exception, a poor nucleophile.

33
Q

Rate the following leaving groups on a scale from 1-4, 1 being the least basic, and 4 being the most basic:
>Chloride
>Carboxylate
>-OR
>-NH2

A

1: Chloride
2: Carboxylate
3: -OR
4: -NH2

34
Q

How do you attempt to have an unfavorable reaction order?

A

-Add excess of nucleophile or use a stronger one.
-Add heat
-Activate Carbonyl (Make stronger electrophile, protonate using an acid)

35
Q

Because I feel that in my bones she will make this extra credit. Provide the mechanism for acetal CoA.

A

Organic Chemistry 2 (14 decks)

Brainscape helps you reach your goals faster, through stronger study habits.
© 2024 Bold Learning Solutions. Terms and Conditions