Exam 2S Review

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antiaroma
tic

nonaromatic

aromatic

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antiaromatic

NH

antiaromati
c

aromatic

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antiaromat
ic

aromatic

aromatic

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Predict the products.

1)

This cation is 2° and 3°. Other cation is 2° and 2°.
Thermodynamic product is most substituted alkene.

H

Br

+

+

Br-

Br

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4)

H

3

CO

O

O

H

3

CO

H

H

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HCl

Cl

+

Cl

+

CO

2

CH

3

CO

2

CH

3

heat

CO

2

CH

3

CO

2

CH

3

+

CO

2

CH

3

CO

2

CH

3

+

O

O

heat

O

O

H

H

+

O

O

H

H

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+

CO

2

CH

3

heat

CO

2

CH

3

+

CO

2

CH

3

CO

2

CH

3

heat

CO

2

CH

3

CO

2

CH

3

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28)

O

ClCOCH

2

CH2CH

2

CH

3

/AlCl

3

Zn(Hg)

HCl

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b
)

ClCOC(CH3)3

AlCl

3

O

NH

2

NH

2

/KOH

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CH3Cl

AlCl

3

CO

2

H

KMnO

4

NO

2

H

2

Pd-C

HNO

3

/

H

2

SO

4

NH

2

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Br

Br

+

CO

2

H

Br

CH

3

Cl/

AlCl

3

Br

2

FeBr

3

KMnO

4

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32.Predit the prodcut.

d)

OH

NO

2

Sn

HCl

OH

NH

2

e
)

OH

O

R

NH

2

NH

2

-OH

OH

R

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35.Predict the products.

a)

NO

2

HO

HNO

3

H2SO

4

NO

2

HO

NO

2

HO

O

2

N

NO

2

b)

OH

SO

3

H2SO

4

HO

HO

SO

3

H

SO

3

H

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c)

O

CH

3

CH

2

Cl

O

Cl

AlCl

3

O

O

Cl

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54c) Fill in the blanks.

Cl

2

FeCl

3

Cl

Cl

O

CH

3

CH

2

CH

2

COCl

AlCl

3

Zn(Hg)

HCl

Cl

1

2

3

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f)

CH

3

Cl

AlCl

3

SO

3

H

2

SO

4

SO

3

H

CO

2

H

SO

3

H

KMnO

4

1

2

3

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j)

CH

3

Cl

AlCl

3

CH

3

SO

3

H

2

SO

4

CH

3

SO

3

H

Cl

2

(excess)

FeCl

3

CH

3

Cl

Cl

SO

3

H

CO

2

H

Cl

Cl

SO

3

H

KMnO

4

1

2

3

4

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k
)

(CH

3

)

2

CHCl

AlCl

3

NO

2

HNO

3

H

2

SO

4

Cl

2

FeCl

3

NO

2

Cl

NO

2

Cl

Br

Br

2

hv

KOCH

3

NO

2

Cl

1

2

3

4

5

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55d)

CH

3

Cl

AlCl

3

HNO

3

H

2

SO

4

O

2

N

CO

2

H

O

2

N

Sn/HCl

CO

2

H

H

2

N

KMnO

4

1

2

3

4

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f)

O

CH

3

CH

2

COCl

AlCl

3

Br

2

FeBr

3

O

Br

NH

2

NH

2

-OH

Br

Br

NO

2

HNO

3

H

2

SO

4

H

2

Pd-C

Br

NH

2

1

2

3

4

5

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AlCl

3

O

CH

3

CH

2

CH

2

COCl

O

O

2

N

HNO

3

H

2

SO

4

NH

2

NH

2

-OH

O

2

N

H

2

Pd-C

H

2

N

j)

1

2

3

4

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O

AlCl3

CH3CH2CH2COCl

Cl

2

FeCl

3

O

Cl

O

Cl

Br

Br

2

hv

O

Cl

HO

-OH

POC

O

Cl

O

k)

1

2

3

4

5

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CH

3

CH

2

Cl

AlCl

3

Br

Br

2

hv

KOR

Br

2

Br

Br

2 NaNH

2

58a
)

1

2

3

4

5

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CH

NaH

b)

C

CH

3

CH

2

Br

1

2

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h)

Cl

2

FeCl

3

Cl

Cl

NO

2

HNO

3

H

2

SO

4

Br

2

hv

Cl

NO

2

Br

Cl

NO

2

KOR

mClPBA

Cl

NO

2

O

H

2

O

Cl

NO

2

HO

1

2

3

4

5

6


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