Võ Lâm Hoài Trung

BTCEIU19009

ORGANIC CHEMISTRY 2
Homework 1
12.30
a. Three compound can be rank the acidity through the induction effect of electron-withdrawing
chloride which can stabilize the conjugated form, so which compound have more chloride near
the hydroxyl is more acidic. The acidic ranking is:
Cl Cl Cl
Cl Cl Cl
< Cl <
Cl Cl
OH OH OH

b. Three compound can be rank the acidity through the salvation effect since these alcohol are all
secondary, so which compound have bulkier structure have less space to interact and be
stabilized by solvent will have less acidity. The acidic ranking is:

> >
OH OH OH

c. Among three compounds, cyclohexanol is less acidic since it have no resonance structure.
With the phenol and m-nitrophenol, the m-nitrophenol have the resonance with the lone pair is at
the carbon atom have link to electron-withdrawing group nitro which help stabilize the structure
and therefore have highest acidic.

O O O

O
O

O O O

NO2 NO2 NO2

O
O

NO2
The ranking is:
OH OH OH
NO2
< <

12.33
[H3O+] OH

H
O H
H H O H

O H H
H O H

12.36
a. O b. O c. O
H

12.38
H
Br O

O
Br O

12.42
O
O H H
O OH

H H
H
H Al H
H
a.
b.
O
O H Me
O OH
H
H
H B H
H