L2- FGI

Question 1

Initiators

Answer 1

AIBN-> N2 and 2x rad

DAPeroxide -> 2x rad-> CO2 and R rad

Question 2

FGI conversions

Answer 2

SCONX
S-S(e)Ph
C-COOH
O-OH
N-NH2/NO2
X-Haliede

Question 3

Simple FGI’s

Answer 3

X,NO2, S(ePH)

NO2 XX primary

Question 4

-COOH

Answer 4

-COOH+SOCl2 -> COCl
COCl +heterocycle -> COON
COON +AIBN/Sn –> RCOO rad –> R rad > RH
also a het-sn

• het cycle 6 member
• N in w oh attatched
• double S outside

Question 5

Barton trapping

Answer 5

CO-ohet + hv/D +XCCl3 -> RX

CO-ohet +tBuSH +O2 -> ROH

(R->ROO->ROOH -> ROOH3 -> ROH +H2O

Question 6

-OH

Answer 6

ROH +base -> RO-
RO- + CS2 +MeI -> ROC(S)Sme
then norm conditions
prod = R rad + double O compound
NB SnBu attacks double bond S

Question 7

-NH2

Answer 7

RNH2 +LG-CHO -> RNH-CHO
RNH-CHO + TsCl, py -> RNC

NORMAL COND
SnBu attacks C

Question 8

Formation of isonitrile

Answer 8

RNHCHO -> RNHCHOTS
OTs leaves and forms RN≡CH
pyr base then takes off h