Amides (-CONH2/ -CONR2) + cyanides (-CN)

prepare amides

1) anhydrous acid chloride + amine (1/2/), room temp (condensation)

hydrolysis amides

1) H2SO4(aq), heat

amide + H+ + H2O:

split at C-N → RCO add OH, N add 2H+ → N becomes N+

2) NaOH(aq), heat

amide + OH-:

split at C-N → RCO add O-, N add 1H

test for 1/pri amide → NH3 turns red moist litmus paper blue

reduction amides

1) LiAlH4 in dry ether, room temp

amide + H4 → C sub O with 2H(sigma bond) + H2O formed

no. of reactions amides

hydrolysis - 2

reduction - 1

hydrolysis cyanides

1) H2SO4(aq), heat

cyanide + H+ + 2H2O → C add OH and O, N add 4H become N+

2) NaOH(aq), heat

cyanide + OH- + H2O → C add O and O-, N add 3H

reduction cyanide

1) LiAlH4 in dry ether, room temp

2) H2, Ni + heat/ Pt + room temp

add 4H across CN

no. of reactions cyanide

hydrolysis - 2

reduction - 2