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Alkyl Halides Carbocation Stability Order - Solved Quiz | CHEM 212, Assignments of Organic Chemistry

Bucknell UniversityOrganic Chemistry

Material Type: Assignment; Class: Organic Chemistry II; Subject: Chemistry; University: Bucknell University; Term: Unknown 1989;

Typology: Assignments

Pre 2010

Uploaded on 08/19/2009

koofers-user-fvm
koofers-user-fvm 🇺🇸

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bg1
N
OOO
OH
H
OHOH
Br OH
Br
OH
Br
Br
Br SMe
IOH
Br OEt
Cl
Chem 212
Alkyl Halide Problems 5 ANSWERS
N3
1. Rank the following carbocations in order of stability from worst to best.
Cl
b)
c)
d)
Br
Br
e)
f)
g)
Br
h)
2. Provide the mechanisms for the following reactions. Clearly show every bond making and bond breaking step.
H2O
Br
H2O
a)
Br
b)
c)
KOt Bu
KOt Bu
I
e) NaSMe
I
KOH
H2O
AgNO3
EtOH
I
h)
g)
f)
Cl
i) NaNH2
j) NaNH2
3. Provide the products of the following reactions:
a)
a)
KOt Bu
d)
b) NaOMe
MeOH
c) NaN3
d) NaNH2
e) H2O
f) KBr
DMSO
NH3
NH3
t BuOH
t BuOH
t BuOH
DMF
NH3
321
13
~ same 1
1~ same
2
O+H
3
H
1
312
H
312
OH
H
213
1
H
3
H
2
..
H2O
..
OEt
H2O
..
H
H2O
..
OH
HOEt
H
..
H
EtOH
..
N3
OH
Br
nearly
racemic
+
major minor
NR
NaN3
H2O

Partial preview of the text

Download Alkyl Halides Carbocation Stability Order - Solved Quiz | CHEM 212 and more Assignments Organic Chemistry in PDF only on Docsity!

N

O O^

O

O

H

H

O

H

O

H

Br OH

Br

OH

Br

Br

Br SMe

I OH

Br OEt

Cl

Chem 212 Alkyl Halide Problems 5 ANSWERS

N 3

  1. Rank the following carbocations in order of stability from worst to best.

Cl

b)

c)

d)

Br

Br

e)

f)

g)

Br

h)

  1. Provide the mechanisms for the following reactions. Clearly show every bond making and bond breaking step.

H 2 O

Br

H 2 O

a)

Br

b)

c)

KO t^ Bu

KO t^ Bu

I

e) NaSMe

I

KOH

H 2O

AgNO

EtOH

I

h)

g)

f)

Cl

i)

NaNH (^2)

j)

NaNH 2

  1. Provide the products of the following reactions:

a)

a)

KO t^ Bu

d)

b) (^) NaOMe MeOH

c) NaN^3

d) NaNH 2

e) H2O

f)

KBr DMSO

NH 3

NH

t (^) BuOH

t (^) BuOH

t (^) BuOH

DMF

NH 3

~ same (^1)

(^1) ~ same

O+

H

H

H

OH

H

H

H

..

H 2 O

..

O

Et

H 2 O

..

H

H 2 O

..

OH

HOEt

H

..

H

EtOH

..

N

OH

Br

nearly racemic

major minor

NR

NaN 3

H2O