L22 - (Oxdiation) And Reduction
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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)