Formations

Question 1

Ald/ket (ROH -> -OR)

Answer 1

Hemiacetal (replace pi O w/ alc and OR)
(Nuc attack, PT)

Question 2

Ald/ket (ROH (xs) <-> acid)

Answer 2

Acetal (replace pi O with OR x2) and H2O
(PT, Nuc, PT, PT, Loss of H2O, Nuc, PT)

Question 3

Ald/ket (H2N- H(R) (xs) <-> )

Answer 3

Imine (replace pi O with pi N-H(R)) and H2O
(PT, Nuc, PT, PT, loss of H2O, PT)

Question 4

Ald/ket (R2NH(xs) <->)

Answer 4

Enamine (1H becomes pi bond (E) and pi O becomes N-R2) and H2O
(PT, Nuc, PT, PT, loss of H2O, PT)

Question 5

Ald/ket (mCPBA -> [H+] H2O)

Answer 5

Carboxylic Acid/Ester
(Adds O between pi bond O and most sub substituent)
H>3•>2•~Ar>1•>methyl

Question 6

Ald/ket (RSH (xs) -> [H+])

Answer 6

Thioacetal (Replace pi O with two S with remainders connected) and H2O

(Reverse with Raney Ni)