Exam #2

Chemistry 215 with Allen/gottfried/wolfe at University of Michigan - Ann Arbor

About this deck

By: Kristina Brooks
Textbook:

Organic Chemistry: Structure and Reactivity
Created: 2009-03-02
Size: 28 flashcards
Views: 293

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What are the members of the acyl family?

-Carboxylic Acid
-Acid chloride
-Acid anhydride
-Ester
-Thioester
-Amide

What is the order of functional group priorities?

1. Carboxylic acid
2. Ester
3. Amide
4. C-N triple bond
5. Aldehyde
6. Ketone
7. Alcohol

What is an acyl group?

What is the structure of carboxylic acid?

What is the structure of an acid (acyl) chloride?

What is the structure of acid (acyl) anhydride?

What is the structure of an ester?

What is the structure of a thioester?

What is the structure of an amide?

-Acetyl Group
-Ethanoyl
-Ac

-Acetate
-Ethanoate
-AcO

-Acetic Acid
-AcOH

-Benzoyl Group

-Benzoate

List the reactivity of leaving groups within the acyl family from highest to lowest.

-Acid chloride (GOOD)
-Acid anhydride (GOOD)
-Thioester (POOR)
-Carboxylic acid/carboxylate (POOR)
-Amide (POOR)

What are the structures of good and poor acyl chloride nucleophiles?

-Acyl chloride itself is a ???

What are the structures of good and poor anhydride nucleophiles?

Good: Na
Poor: H

Attached to carboxylic acid.

What are the structures of good and poor thioester nucleophiles?

Good: Na
Poor: H

Attached to SCH3.

What are the structures of good and poor carboxylic acids or carboxylates?

Good: Na
Poor: H

Attached to OH or OCH3, respectively.

What are the structures of good and poor amide nucleophiles?

Good: excess NH3
Poor: ---

How many times do nucleophiles usually attack a carbonyl? What are the exceptions?

-They only attack once

-Exceptions: C & H nucleophiles attack twice

What is the basic mechanism in the formation of carboxylic acid derivatives?

1. Proton Transfers (Protonate)
2. ATTACK
3. Proton Transfers
4. REFORM
5. Proton Transfers (Deprotonate)

Is it necessary to have three proton transfers in the reaction to form carboxylic acid derivatives?

No, there is a maximum of three proton transfers throughout the entire mechanism. The amount varies upon conditions.

When do you need a proton transfer before the attack of the carbonyl?

-Protonate less reactive carbonyl groups, such as: esters and amides
-Do not protonate acyl halides or anhydrides
>Highly reactive and electrophilic

Why do you need a proton transfer between attacking and reforming the carbonyl?

Ensures that the leaving group is compatible with the conditions.

When do you need a proton transfer after the reformation of a carbonyl?

In order to form the final product.

What is the mechanism for regular nucleophilic attacks of acyl halides?
How do H & C nucleophiles differ in their mechanisms?

1. Attack
2. Reform
3. Deprotonate

1. First attack
2. Reform
3. Second attack
4. Protonate

Can a carboxylic acid be transformed into an amide? If so, then how?

-No. You can NOT change a carboxylic acid into an amide

About this deck

By: Kristina Brooks
Textbook:

Organic Chemistry: Structure and Reactivity
Created: 2009-03-02
Size: 28 flashcards
Views: 293

About StudyBlue

“I have been getting MUCH better grades on all my tests for school. Flash cards, notes, and quizzes are great on here. Thanks!”
Kathy