19

Question 1

NaBH4 in CH3OH

Answer 1

ketone –> secondary alcohol

Question 2

1. BH3 THF 2. H2O2, NaOH

Answer 2

alkene –> primary alcohol

Question 3

TsCl in Pyridine

Answer 3

alcohol –> OTS

Question 4

LDA in THF

Answer 4

leaving group to alkene

Question 5

PCC in dry CH2Cl2

Answer 5

primary alcohol –> aldehyde

secondary alcohol –> ketone

Question 6

Acyl chloride and AlCl3

Answer 6

acylation

Question 7

H2CrO4 in H2O

Answer 7

ketone –> carboxylic acid

Question 8

SoCl2

Answer 8

OH –> Cl

Question 9

LiAlH(OtBu)3 , H2O

Answer 9

acyl chloride –> aldehyde

Question 10

1.DIBAL - H in hexane, -78 ,2. H2O

Answer 10

ester/nitrile –> aldehyde

Question 11

nBuli

Answer 11

deprotonate, cation

Question 12

after nBuli what can u do

Answer 12

throw ketone (creates anion oxygen), throw R-Br (creates ester)
BrCh2Ch3 or any Br-R (add methyl or ethyl group onto acetal group) (adds substituents)

Question 13

Gilman reagent, (R)2CuLi, H2O

Answer 13

R group replaces leaving group

Question 14

NH2-R, adjust ph dilute H3O+

Answer 14

N replaces O makes amide, R group attaches to N

Question 15

1. R-MgBR 2. Excess H3O+

Answer 15

1 adds R to nitrile 2 nitrile –> ketone

Question 16

PPh3-R in THF, -78 degrees to 0 degrees

Answer 16

R replaces oxygen instead of ketone

Question 17

Dithiol, H2SO4

Answer 17

protects aldehyde and ketone

Question 18

TMSCl, NEt3

Answer 18

protects alcohol group

Question 19

NaF, NH4Cl

Answer 19

undoes protection from TMS

Question 20

HgCl2, H2O

Answer 20

undoes protection from dithiol makes ketone or aldehyde

Question 21

1. Ch3MgBr, 2. H3O+

Answer 21

aldehyde –> methyl and alcohol

Question 22

H2SO4, KCN OR HCN

Answer 22

ketone -> nitrile and alcohol

Question 23

:PPh3 in DMF , nbuli

Answer 23

P cation and leaving group eliminated, double bond with cyclic and pph3

Question 24

H20 catalytic H2SO4, PCC in dry Ch2Cl2

Answer 24

alkene –> alcohol -> ketone