CHEM U332 Spring 2021

Professor Ruppel
HW4B; Due: Thursday 2/11 @ 11:59pm

Quoc Vo
Cuong
Name: _____________________________________________________________________________
In the spaces provided below, predict the major product(s) of the reactions shown. On a separate piece(s) of
paper draw out the any pertinent mechanisms to explain the transformations. Submit both the products and
mechanisms via Bb.

fifty
O

H O H
N -
°
-
'
E E
'

OCH3 I OCH

⇐T"
E
,

O * T m
'

T
Ph
E

E
t" A- E
NH2 Nk tBu
E E
H3C \ CH3
% on
,

CF Cl n
U
CF3
E E ,
-
l O 2N t
O N E
E 2

Out
,
OCH3 H3C
X -
en CR E
, ,

±
.

he
CH3 E E
H3CO '
"
O cry o

Furan, a heterocyclic aromatic compound, readily undergoes EAS type reactions. In the spaces below,
determine which of the two products shown is the “major” product and which is the “minor” product. Provide a
detailed mechanism and a brief explanation to support your conclusion.

O O + O
E
E

minor
major

¥
[n I
E)
'

een e' :-D,

no ,
, -

major
⑦ - E
← ⇐

3 Resonances

t.in )
i
: ⇐ Y m
'
E

2 Resonances
 % .

÷÷¥±
→ ~
.

"'
✓
"
¥f9¥ .

E
an
.

~ TT :B
m.
,

,
%

A t"
ton . :B
n'
Ef
,

n
.

¥÷¥
"
I
:D
.

FE
E
 !
a

?
- "
' ' '
✓ µ
,

an

Ohh
,
out

¥45
,
:B

✓ Then
'

✓
,

En i

¥÷÷i
'=

.
.

A ca IET :B
,
uh
he
-
>

'
" '
cry o ang "
o