315 hw5 ans

Homework Set Chem 315 Beauchamp 1. This collection of RX compounds and reagents will generate 40 SN/E problems. You s...

4 downloads 86 Views 77KB Size
Homework Set

Chem 315

Beauchamp

1. This collection of RX compounds and reagents will generate 40 SN/E problems. You should be able to predict reasonable products (major and minor) for each of them. Use structure C to write reasonable mechanisms for the SN/E reactions of reagents 2, 4, 5 and 6. RX Compounds H

T C

C

H D

H

A

H

D

4

O

make

H Li H

Na

Al

H

H

make

Li

C

Na

Na

Na

buy

make

make

CH2

S

Na

H buy

O

7

10

9

N

Br

O O

make

O

6 N

K

make

8

D

D

5

O

O

Na

Na buy

H3C

Br

C

B

O

H

Br

Nucleophile/Base Compounds 3 2 1 H

D

C

H3C

Br

H

D

buy

2. Write out detailed mechanisms for the tautomer reactions below. Hint: How many protons have changed positions? a

H O O

O

C H3C

C H

H

H

H O

H

H

O O

C H H3C

H

b

O

O

C

C

H3C

H

H H

NH2 O

O

O

SH

O

OH O

C

OH O

N

Z:\classes\315\Daily Homework Sets\315_hw5.doc

H

H

O

C H3C

3. Nomenclature problem

H

O

C H

H

H

O

O

H

C H

H H

Homework Set

Chem 315

Beauchamp

The elimination products are the same for all the strong nucleophile/bases and are shown below. H

T C

None, only SN2 is possible.

Br

H D

C H

H

Br

H

C

C

C

H

H

H3 C

H

D

H

A Only SN2

buy

SN2

Na

HO

C

O

Na

make

O

H3C

Br

D

Br

D

E2 > SN2 H

OH

D Only E2

D

H

HO

D

SN2 > E2

T

H

C H

Only SN2

D

H

E2 > SN2 O

H

D

C H3C

H

SN2

C

D

Only E2

C H

D

H D

O

H

T

3 O

O

K

C

SN2

H

O

4

Na O

make

O

Only SN2 O

C

S N2

O

C

H3C C

SN2 > E2

T SN2

N

C

C

make

C

H

D

Only E2 N

D

SN2 > E2

Only SN2 H3C

C

D

H H

S N2

H

C

H 3C

H D

Na

SN2 > E2

C

C

buy

6

Only E2

H

O

D N

Only SN2 C

D

D

H

5

H

O

H D

H

Na

Only E2

SN2 > E2

SN2 > E2

T

O

N

Only E2

mainly E2

D

make

CH3

T C

H H

D

CH3 C

C

D

C H

C C D

Z:\classes\315\Daily Homework Sets\315_hw5.doc

mainly E2

C CH2

H3C

H 3C

C

C

D

2

H

D

H3C

H

H 3C

CH2 CH3

H

C

D

C

Br

SN2 > E2

T

C H3 C

DHC

B

Nucleophile/Base Compounds O

H

C C

H

H

CH3

C

D

H3C

CH2 CH3

C

H

CH3

C

H 3C

CH3

Br

C H

H3 C

DHC

T C

CH3

C

H 3C

RX Compounds

1

C

CH2

D

Br

C

H 3C

H H 3C

H D

CH2

CH3

CHD

C

C

DHC

CH3 H 2C

Only E2

H

H

C

DHC

D

D

C

CH3

CH3 H

C H 3C

H3C

B

D

D

C

H 3C

C

H3 C

D

Br

H

D

H

C

C

H3C

A H

H

D

Only E2

CH3

Homework Set

Chem 315

7

Only SN2

O

Li make

C

SN2 > E2

O

S N2

N

H

H

H

H

Al

D

SN2 > E2

H

H

H3 C

C

H

SN2 > E2

SN 2

Na

HS

H

SN2 > E2

D

H

Only E2 D

H

D

H

C C

H

buy

H

SH

H3 C

C

not covered in our course

D

SN2 > E2

T

D

D

H H

Only SN2 S

H

C C

D

10

a

O

T SN2

Only E2

H

N

D

Only SN2

H

H

O

C O

H buy

N

C H

O

Li

D

CH3

C D

9

H

SN2 > E2

O

Na O

O

D

T

make

D

H

Only SN2

O

Only E2

H

C

H3C H

N

D

H D O

8

H

SN2 > E2

C

SN 2

CH2

O

SN2 > E2

T

Beauchamp

HS

D

H

O O C

O

O

H3 C

C

H C

H

C

O

H3 C H

H

O

H C

H

H H

O

O

H

O

H3 C

C

resonance

H

H

O

C

H

H3C

O C

H

H

H

O

Requires two tautomeric cycles. H

H H

O

O

O

Acid reaction not shown.

resonance C O

C H3C

H

C

O

H

H3C

C

O H3C

C

H

H

H H

5

4

2 3

1

4 3 2 1

NH2 H

12

10 11

O

5 6

9

O

8 7

6

OH

4 3

5 O

O 2

1

SH

O

1

2

C

4 3 OH

O

H

N 3R-mercapto-4S-hydroxy-4-phenylbutyl (2R,3R,10R,11S)-2-formyl-3-propoxy-4-cyano-6,12-dioxo9-(3-pentyl-6,6-dimethylcyclohex-3-enyl)-10-hydroxy-11-aminododec-4E-en-7-ynoate

Z:\classes\315\Daily Homework Sets\315_hw5.doc

O C

H