Chem 345 PSet 08 key

Draw the mechanisms for the following transformations: A... What is the shape of the signal of the indicated proton singlet, doublet etc…?. Br Br sextet singlet quartet CH's are enantiot

Chem 345 PSet 08 Key

1.) Draw the mechanisms for the following transformations:

A

O

2.) H3O+

Ph

Ph OH

OH +

B

OH

Et2O 2.) H3O+

Ph O

N

Ph

O

1.) PhMgBr, Et2O 2.) H3O+

1.) LiAlH4, Et2O 2.) H3O+

O

OH

1.) LiAlH4, Et2O 2.) H3O+

O O

1.) LiAlH4, Et2O 2.) H3O+

OH O

OH

1.) LiAlH4, Et2O 2.) H3O+

N H

O

N H

2.) Write the mechanisms for the following reactions:

O

O

O H

O O

O

Δ

NH2OH, HCl

H2SO4, H2O

N H O

3.) What is the shape of the signal of the indicated proton (singlet, doublet etc…)?

F

Br Br

sextet

singlet

quartet

CH's are enantiotopic,

so they do not visibly split one another

CH2's are homotopic,

so they do not visibly split

one another

doublet of doublets of quartets

J=14,10,7,7,7

4.) Fill in the boxes If multiple steps are needed, be sure to use 1.) and 2.) to differentiate different steps Be sure to watch where the arrow points

O

NH

O

1.) Δ, NH2OH, HCl,

H2SO4, H2O

2.) LiAlH4, Et2O

3.) H3O+

1.) RCO3H (or other peracid like mcpba) 2.) LiAlH4, Et2O

3.) H3O +

Baeyer-Villiger followed by LAH reduction

Beckmann followed by

LAH reduction