CHEM 2444-03 Organic Chemistry II Worksheet #7: Carbonyl Additions

M W Peczuh

1. Provide structures for A – K. (22 points, 2 points each)

O
i)Ph-MgBr H2SO4
ii) H3O+
A B
heat

O
Ph3P CH3 Br
H
nBu-Li
C

O
mCPBA
D

i)Ph-MgBr H2SO4(cat)
O C O
ii) H3O+
E F
CH3OH

O NH2

i)NaBH4 PBr3 NaCN i)LiAlH4

ii) H3 O+
G H CH3CH2OH
I ii) H3O+

O
H+ (cat) i)allyl-MgCl
J K
H CH3NH2 ii) H3O+
 2. Show how to convert cyclopentanone to the compounds shown. You may use any other
reagents/conditions necessary to complete the syntheses. (5 syntheses, 3 points each = 15 points total)

O
H3CO OH
O O
OH Cl

O
H3CO OH
O O
Cl

H3CO OH
Cl O

H3CO OH
Cl O

OH
O
3. Provide structures for L – P.(15 points, 3 points each)

1) MgBr ; H O+
3

O 2) PCC L
3) MgBr ; H O+
3

1) NaNH2
2) acetaldehyde; H3O+

3) PCC
M
4) CH3MgBr; H3O+

1) H2SO4(cat), H2O
2) H2CrO4
N
3) CH3CH2NH2
4) NaBH4
5) benzoyl chloride

1)KOtBu
Br 2) OsO4, NMO
O
3) H2SO4(cat), acetone

1) Br2, FeBr3
2) Mg(0)
3) CO2; H3O+
P
4) SOCl2 NH2
5) 2 eq.

6) LAH; H2O