Chapter 20

Question 1

Oxidation [o]

Answer 1

-increase in C-EN
-Decrease in c-h

Question 2

Reduction [H]

Answer 2

-decrease in c-en
-increase in c-h

Question 3

Alkene Reduction

Answer 3

Reagent: H2/Pd
-adds 2 H bonds across double bond syn

Question 4

Alkyne Reduction

Answer 4

Reagent: H2/PD or Lindlar
-reduces all the way to a single bond if H2/PD
-reduces to a cis alkene is Lindlar

Question 5

H2 limitations

Answer 5

-Can reduce aldehydes (oh)
-Cannot reduce ketones or Esters

Question 6

Reduction of C double O to CH2

Answer 6

Clemmenson
-reagent: Zn(HG)/hcl
-use when avoiding OH
-only reduces aldehydes and ketones
-(leaving group Br, Cl)

Wolf-Kischner
-Reagent: Nh2-NH2/ NaOH
-use when avoiding H (sperate double bond)

Question 7

Oxidation of Alcohols and Aldehydes

Answer 7

Reagents: PCC or H2CrO4 (other cros)

PCC: oxidizes 1 and 2 alcohols
H2CrO4: oxidizes 1 and 2 alcohols and aldehydes

-primary alchohol: pcc stops at aldehyde but other goes to carb

-secondary alcohol: pcc and H2Cr go to a ketone

-Aldehyde: goes to carb acid with H2CrO4

Question 8

Organometallic Coupling

Answer 8

Reagents: R2CuLi (gilman)
-couples with r-x to form a new c-c bond
-R-x must be methyl, 1, 2, sp2

Question 9

Organometallic Coupling (Organomagnesium or Organolithium)

Answer 9

Reagents:
-RMgBr (gringard)
-RLi (oithium)

-attacks electrophillic and adds R group to spot it attacks
-If O was present it gets turned to an OH
-If n is present it gets turned into a ketone

Question 10

Palladium Catalyzed Coupling

Answer 10

-Suzuki and Heck

Question 11

Suzuki

Answer 11

-sp2 R-x + R’-B(or)2 with Pd(PPh3) catalyst

-r bonds bond together and stay in cis/trans formation

Question 12

Heck

Answer 12

• Sp2 r-x couples with less sub alkene c
  -catalyst is Pd (OAC)2