Chapter 6: Carbonyl Chemistry

Question 1

What are the requirements of an SN2 mechanism? (Reactivity, Stereochemistry, Kinetics, Solvent, Rearragenments and Favoring conditions)

Answer 1

Prefers less crowded attack areas 
Inversion of Stereochemistry 
kinetics relies on both the electrophile and nucleophile 
performed in an polar aprotic solvent 
No rearrangements occur 
Strong, non-bulky nucleophiles

Question 2

What are the requirements of an SN1 mechanism? (Reactivity, Stereochemistry, Kinetics, Solvent, Rearragenments and Favoring conditions)

Answer 2

Prefers more substituted carbocation to provide inductive stability.
The stereochemistry becomes a racemic mixture.
Kinetics only involve the use of the electrophile
Done in polar protic solvents
Rearrangements can occur
Weak nucleophiles.

Question 3

Examples of polar protic solvents?

Answer 3

Acetic acid, water, alcohols, and amines

Question 4

Examples of polar aprotic solvents?

Answer 4

DMF, DMSO, acetone, and ethyl acetate

Question 5

Can primary alcohols be oxidized?

Answer 5

PCC makes them into aldehydes, anything else makes it into a COOH

Question 6

Can secondary alcohols be oxidized?

Answer 6

Yes by any oxidizing agents into ketones.

Question 7

Review the mechanism of Acid and Base catalyzed keto and enroll tautomerization

Answer 7

Draw the mechanism

Question 8

Which is more stable the ketone or the enol? Why?

Answer 8

The enol is less favored due to the presence of the C=C where the C=O bond is favored.

Question 9

What can NaBH4 reduce?

Answer 9

aldehydes and ketones

Question 10

What can LiAlH4 reduce?

Answer 10

aldehydes, ketones, COOH, and esters

Question 11

How are Gringard reactions followed through?

Answer 11

They are reacted with magnesium, and then allow for a addition to the carbonyl in the presence of a aprotic solvent. Then treated with acid.

Question 12

What is the purpose of mesylates and tosylates for alcohols? For carbonyls?

Answer 12

Alcohols serves the purpose of acting as a leaving group for substitution, while for carbonyls allows for their protection.

Question 13

Review the mechanism of creating acetals from acid and alcohol

Answer 13

Mechanism drawn in notes.

Question 14

Review the mechanism of creating cyanohydrins

Answer 14

Mechanism drawn within notes.

Question 15

Review the mechanism for Imine and Enamine formation. What is required?

Answer 15

ACID present must allow for the reaction to proceed.