L22 - (Oxdiation) And Reduction Flashcards
How can you convert a nucleophile intro an electrophile?
By oxidising it
What happens when you reduce a ketone?
You get a secondary alcohol
What happens when you reduce an aldehyde?
You get a primary alcohol
What is an example of a mild reducing agent?
NaBH4
How do you reduce an aldehyde with NaBH4?
- e- density in an H-B bond attacks carbonyl C
- breaks db = O-
- intermediate formed
- H from HA attaches to O-
= alcohol
How do you convert an acetophenone into a benzyl alcohol?
- NaBH4 EtOH
- Acid
What are the steps in the reduction of carboxylic acid derivatives?
- e- density in H-Al attacks carbonyl C
- db breaks = O-
- O- kicks out OR’
- happens again
- O- to HA
= Alcohol
What is an example of a powerful reducing agent?
LiAlH4
Et2O
What reacts with NaBH4 from the rank order?
- acyl chloride
- acid anhydride
- aldehyde
- ketone
What reacts with LiAlH4 from the rank order?
- acyl chloride
- acid anhydride
- aldehyde
- ketone
- ester
- amide
How to convert nitrile into amine?
LiAlH4
Et2O
How to convert amide to amine?
LiAlH4
Et2O
How to turn alkene to alkane?
H2
Pd/C
How to turn alkyne to alkene?
H2
Lindlar catalyst Pd/C
Why are alkynes only converted into cis/Z alkenes?
H-H can only adsorb and bind to one side
How do you convert NADH/NADPH to NAD+/NADP+?
[R] of C=O
- lp on N attacks bond
- moves db to next bond
- e- density in C-H attacks carbonyl C
- H transfers to O-
How do you convert NAD+/NADP+ to NADH/NADPH?
[O] of R-OH
- H-O bond attacks C-O bond
- C-H bond attacks C in ring
- moves db to the next
- bond moves to N+
What does NAD(P) stand for?
Nicotinamide adenine dinucleotide (phosphate)
