A2 nucleophillic addition Flashcards
c=o bond
carbon is positive and oxygen is negative. the C is attacked by nucleophiles. The shape is trigonal planar shaped so the c and o and the two other atoms are joined to the c and in the same plane. Reagants react across the double bond
Reagant in nucleophillic reaction reduction
NaBh4
conditions
aqeous
what happens
2 H atoms bond to c and o
products
primary alcohols from aldehydes secondary alcohols - ketones
c=o rotation
the bond cannot rotate p orbital electrons overlap forms a pie bond above and below the double bond causes restricted rotation
why are aldehydes more likely to undergo nucleophilic addition
there are fewer carbonyl groups means less positive inductive effect and electrons supplying electrons. This is increases positive charge
steric effect in nucleophillic addition
In aldehydes, the relatively small hydrogen atom is attached to one side of the carbonyl group, while a larger R group is affixed to the other side. In ketones, however, R groups are attached to both sides of the carbonyl group. Thus, steric hindrance is less in aldehydes than in ketones.
what provides what
water gives h+ and h- is given by NaBh4-
mechanism
addition of HCN conditions
aqeous
Nitrile reagant
KCN and acid
what happens in CN
CN adds onto the c=o C and H adds onto the O of the C=O
Mechanism of CN
Where does the CN and the H comes from
KCN and acid