Chapter 13 reagents

Question 1

Alcohol with base (

Answer 1

Alkoxide (RO-)

Question 2

NaOH with alkyl halide

Answer 2

Subs

Question 3

alkene plus h2o

Answer 3

sub

Question 4

Alkene plus 1. HgOAc2 2. H2O 3. NaBH4

Answer 4

Adds OH at mark

Question 5

1. BH3 2. THF, OH with alkene

Answer 5

Anti mark OH

Question 6

Cold, dilute KMnO4, OH-

Answer 6

Syn OH across db

Question 7

r-3x 1. THF 2. H3O+

Answer 7

Adds OH to mark

Question 8

Carboxylic acids, esters, and acid chlorides react with Grignards to make

Answer 8

trisub alcohols

Question 9

Grignard

Answer 9

1. RCoX
2. H3O+

Question 10

TMSCl, TEA

Answer 10

subs for OTMs

Question 11

How to change halide to Grignard?

Answer 11

Add Mg, then ether

Question 12

Take off protecting group (TMS) by

Answer 12

H3O+

Question 13

What is a gilman reagent?

Answer 13

R2CuLi

Question 14

What can you use to add R to RX?

Answer 14

R2CuLi

Question 15

NaBH4

Answer 15

Mild reducing agent (works on ketones/aldehydes, not esters/acids)

Question 16

LAH

Answer 16

Strong reducing agent- works on everything

Question 17

How do you open an epoxide?

Answer 17

Grignard

Question 18

How to get grignard to alcohol

Answer 18

H3O_

Question 19

Remove 1 DB

Answer 19

H2, raney nickel

Question 20

Sodium dichromate+sulfuric acid

Answer 20

CHromic acid

Question 21

Alcohol to aldehyde

Answer 21

PCC (mild ox)

Question 22

NaOCl, H2O

Answer 22

Oxidizes alcohol

Question 23

CuO, heat

Answer 23

Ox alcohol (mild

Question 24

Swern

Answer 24

Mild ox

Question 25

Cleave diols

Answer 25

HIO4

Question 26

Makes glycols

Answer 26

OsO4, H2O2

Question 27

Turn OH to good LG

Answer 27

TsCl

Question 28

Add Br to alcohol

Answer 28

PBr3