Core chem 1

Question 1

What reagent/s is required to turn an alcohol into tosilate leaving group?

Answer 1

TsClPy

Question 2

Tosilate to Cyanide reagents? What kind of substitution?

Answer 2

NaCN, DHF
SN2

Question 3

Tosilate to alkyl bromide? Kind of Substitution?

Answer 3

NaBr, acetone
SN2

Question 4

Tosilate to azide?

Answer 4

NaBr, acetone
NaN3, MeCN
2 x SN2

Question 5

Alcohol to alkyl bromide?

Answer 5

PBr3

Question 6

Alcohol to ether?

Answer 6

NaH (B), R’-I

Question 7

Ozonolysis Reagents?

Answer 7

1) O3
2) Me2S, DMS

Question 8

Epoxide Formation?

Answer 8

MCPBA

Question 9

Diols from epoxides?

Answer 9

NaOH (cis and trans)
OR
H+, H2O (just trans)

Question 10

Alcohols from alkenes?

Answer 10

1) Hg(OAc)2, H2O
2) NaBH4

Question 11

Hydroboration alcohol formation?

Answer 11

1) BH3
2) H2O2, OH-
Repeat when necessary

Question 12

Reductive animation
Ketone —> Imine —> amine

Answer 12

1) R’NH2, NaCNBH3
2) NaCNBH3

Question 13

Imine formation
Ketone —> Imine

Answer 13

H2N-R
AcOH