Carboxylic Acid Derivative Synthesis

Question 1

What 2 things can you do to an OH (alcohol)?

Answer 1

SOCl₂: Turn it into a Cl; good leaving group

Jones Reagent: Oxidize into carboxylic acid

Question 2

What can Et₂CuLi do?

or

What can R₂CuLi do?

What can (any ring)₂CuLi do?

Answer 2

Replace a Cl with 1 Ethyl group

or R group

Or ring group

(Add a Cl with SOCl₂)

Question 3

What reagents do you need to add Mg to a Br on a structure?

Answer 3

Mg, Ether

Question 4

Can you add R-MgBr to a carbonyl carbon?

What reagents?

What do you need after to protonate the carbonyl oxygen?

Answer 4

Yes, 2 equivalents if necessary

R-MgBr

H₂O

Question 5

Why would you want to add CO₂ to a carbonyl?

What reagents?

Answer 5

To add ONE extra carbon to the structure

CO₂, H₂O

Question 6

What reagents do you need to add OMe to a carbonyl?

(after you added a carbonyl via CO₂, H₂O)

Answer 6

H₃O⁺, MeOH

Question 7

What does Jones reagent do?

Answer 7

Takes an alpha Hydrogen and turns it into a Carboxylic acid

Question 8

What reagents do you need to make an Amide from an alcohol?

Answer 8

1. SOCl₂
2. NHR₂ or NH₂R (2 equiv)

Question 9

What reagents do you need to make an Amide from an acid chloride or ester?

Answer 9

2. NHR₂ or NH₂R (2 equiv.)

Question 10

What does LiAlH₄, H₃O⁺ do?

Answer 10

Reduce the O= to -OH

Kick out the LG and at 2 H’s