The Web of Reactions - I

Functional Group Manipulation Without Changing the Number of Carbons

Now that we have covered a number of functional group interconversions, it is a good time to integrate them into a larger picture. The n-butane derivatives below are arranged in increasing oxidation level from bottom to top. Make a hard copy of the chart (click on it) and connect the structures with arrows and reagents. Every time you cross a horizontal line, you have done an oxidation or reduction. You will build a web of reactions that will allow you to answer, e.g., how do I make R from L? Below the structures is a list of reactions. Connect the structures with arrows and reagents. Except for one case noted, each reaction can be completed in one step. The list is not necessarily all inclusive. Add your own. When you are finished, try Web of Reactions-II.

From

To

C

D

C

L

C

K

D

C

C

B

D

B

D

M

K

J (two ways)

L

J (two ways)

J

N

(R)-J

(S)-N

N

K

M

P

P

O

O

P

K

H

L

H

M

S

K

G(d,l)

L

G(meso)

G(meso)

F(trans)

G(d,l)

F(cis)

K

A(2R*,3S*)

A(2R*,3S*)

F(trans)

A

R

F(trans)

G (meso)

F(cis)

G(DL)

K

Q

L

Q

C

Q

O

E

E

Q

B

J

J

B

S

D

S

M

P

T

T

P

P

U

T

U