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

Chapter 20-Carboxylic Acids and their Derivatives Flashcards

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1
Q

Suffix for Carboxylic Acid (IUPAC Nomenclature)

A

“-oic acid”

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2
Q

What geometry do carboxylic acids have?

A

Trigonal Planar

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3
Q

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

A

Amphiphilic when chain is longer than 4 carbons.

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4
Q

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

A
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5
Q

Suffix for Carboxylate ion (IUPAC Nomenclature)

A

“-oate”

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6
Q

pKa of Carboxylic Acids

A

~4-5

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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.

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8
Q

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

A

EWGs in crease the acidity.

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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)

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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

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11
Q

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

A

-CO2
-H3O+

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12
Q

Provide a saponification mechanism for the following reaction.

A
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13
Q

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

A

LAH and H3O+

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14
Q

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

A

1) Aldehyde
2) Alcohol

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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.

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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)

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