Facts

Question 1

Nu Addition to epoxides under basic conditions

Answer 1

Addition to less hindered carbon

Question 2

How to make terminal enolates?

Answer 2

LDA

Question 3

Conversion of alcohols to alkyl halides without rearrangement?

Answer 3

PBr3

Question 4

-OH oxidation to aldehyde

Answer 4

Swern: COCl2, DMSO, Et3N

Or PCC. Can also use DMP

Question 5

Reduction of esters to -OH

Answer 5

LiAlH4, acid

Question 6

-OH to RH

Answer 6

Barton Mccombie deoxgygenation (radical reaction, Bu3SnH)

Question 7

-OH to RH ? (Not BMO)

Answer 7

Change OH to good LG with Ts. Reduce with LiAlH4

Question 8

Vicinal diol cleavage products? Reagent?

Answer 8

Forms two carbonyls, NaIO4

Question 9

Reductive epoxide ring opening?

Answer 9

H on more substituted carbon, OH on the other

Question 10

Activation of terminal carbon of alkynes?

Answer 10

LDA(to R-Li)

Question 11

R-R’ bond from R-X?

Answer 11

React with grignard R’MgX

Question 12

Diff between reduction by LiAlH4 and NaBH4?

Answer 12

NaBH4 selectively reduces aldehydes and ketones in the presence of esters. LiAlH4 goes all the way.

Question 13

Activation of terminal carbon of alkynes

Answer 13

LDA

Question 14

Removal of Cbz, Boc and Fmoc respextively?

Answer 14

Hydrogenation, Acid, 1• and 2• amines.

Question 15

Base catalyzed hydrolysis of esters (saponification).

Answer 15

Changes ester to -COOH and -OH. Carbonyl carbon is turned to the acid

Question 16

Reduction of (esters) lactones with LiAlH4?

Answer 16

Yields diol from lactone and two alcohols from acyclic esters