Copyright, 2015, Professor Michael Rathke.

What is the profile of a sports communicator?

No part of this Exam may be reproduced or transmitted without written permission.  (21 total points)

1. Draw the structure of the following compounds:

a) benzyl alcohol

b) o-bromobenzoic acid

c) m-nitroaniline

d) 2,5-dimethyl-1,4-hexadiene

e) p-methylphenol

2.(3 pts. each, 6 points total).  

(3 pts.) (3 pts.) (3 pts.)

(3 pts.) (3 pts.)

Encircle the two compounds which are expected to be aromatic according to Hückel’s Rule: H H H

C

C

H H

C

(-) (+)

C

(+)

N

C C

N

B H H

H H DC

A E

H

C

(-)

CH2 CH CH CH CH CH2 

C C

H H F

G

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (18 total points)

How can you recognize the growth of the Sports industry?

3. Draw appropriate structures in the boxes:

CH3 

a)

CH3 

HBr

(3 pts.) (3 pts.)

two resonance structures of intermediate carbocation

HBr

(3 pts.) (3 pts.)

+

1,2 product 1,4 product

(3 pts.) b) Don't forget about the age old question of darren zook berkeley

Which product will be the major product under conditions  

of thermodynamic control?

(3 pts.) c)

Which product of the above reaction (the 1,2 or the 1,4) will  

be the major product under conditions of kinetic control?

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(9 total points)

4. Complete the following Diels-Alder reaction:

3 pts. 3 pts.

+

Diene Dienophile

O

C

C

CCN O

CH3 

5. Anthocyanins are responsible for the red, purple and blue colors of many flowers, fruits  and vegetables. In an acidic solution, anthocyanins have structure A, below, and in a  basic solution structure B.

What is the growth/magnitude of the Sports industry?

HO

OH

O

R

OH

R

OH

OH

HO

OH

+

O

R

OH

R

OH

Basic solution A

Acidic solution B

One form is colored and the other form is colorless. Which form (A or B)  would you expect to be colored? 3 pts. If you want to learn more check out public policy refers to the outputs of governmental institutions

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (15 total points)

6.

a)

Give the symmetry (symmetric or antisymmetric) of the indicated molecular orbitals  of the following conjugated systems: Don't forget about the age old question of amy saldana fiu

b) c)

3 pts.

3 pts. 3 pts.

HOMO of the excited state Don't forget about the age old question of joanna goger

LUMO of the excited state HOMO of the ground state

Will the stereochemistry of the methyl groups be cis or trans in the product of the  

7.

following electrocyclic reaction?

(Wavy lines mean  

stereochemistry  

unspecified) C 

C

H CH3 

H CH3 

answer

CH CH3 3 3 pts.

8. Will the following suprafacial cycloaddition occur thermally (Δ) or photochemically (hυ)?

+

O O

O

O O

O

3 pts.

answer (Δ or hυ)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(30 total points)

9. Draw the structure of the major organic product:

a) (3 pts.) 

(3 pts.)

CH3 

+

CH3CHBr

AlBr3 

KMnO4 

b) (3 pts.) (3 pts.) SO3H

HNO3 

H2SO4,

10. Draw an appropriate structure in each box:

Zn, HCl

a)

NO2 

O O 

N

(3 pts.) (3 pts.)

Br

CH2CH2CH3 

(NBS),  peroxide

Carbon Radical Intermediate (one resonance structure)

Major Organic Product

b) (3 pts.) O CH2CH3 

C

Br2 

FeBr3 

Carbocation Intermediate

(one resonance structure)

(3 pts.)

Major Electrophilic  

Substitution Product

c)

Cl

NO2 

NO2 

NaOCH3 

Carbanion Intermediate

(one resonance structure)

(3 pts.) (3 pts.)

Major Nucleophilic  

Substitution Product

Copyright, 2015, Professor Michael Rathke. Don't forget about the age old question of asu ecn 221

No part of this Exam may be reproduced or transmitted without written permission.  

(7 total points)

11. Draw the structure (include all H’s in your drawing) of the organic intermediate in the following reaction.

(3 pts.) Br

NH2 

NH2

NaNH2, NH3 

+

CH3 

organic intermediate

12. Outline the steps to complete the following synthesis:

CH2CH2CH2CH3 

Make: From: Cl

(4 pts.)

and any other desired reagents

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (21 total points)

1. Draw the structure of the following compounds:

a) benzaldehyde

b) p-bromoaniline

c) 4-methyl-1,3-pentadiene

d) p-isopropylphenol

e) o-nitrobenzoic acid

2.(3 pts. each, 6 points total).  

(3 pts.) (3 pts.) (3 pts.)

(3 pts.) (3 pts.)

Encircle the two compounds which are expected to be aromatic according to Hückel’s Rule:

H(-)

H H

HH

CH (-)

C

(-)

CH

C

(+)

A

N

H CB

H(-)

F

C C N

H H H D E

CH2 CH CH CH CH CH2 G

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (18 total points)

3. Draw appropriate structures in the boxes: a)

CH3

CH3 HBr

(3 pts.) (3 pts.)

two resonance structures of intermediate carbocation

HBr

(3 pts.) (3 pts.)

+

1,2 product 1,4 product

b)

Which product will be the major product under conditions  of thermodynamic control? If you want to learn more check out econ 2102

Which product of the above reaction (the 1,2 or the 1,4) will  

c)

be the major product under conditions of kinetic control?

(3 pts.) (3 pts.)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(9 total points)

4. Complete the following Diels-Alder reaction:

3 pts. 3 pts.

+

Diene Dienophile

O

C

C OCH3 

CC O

OCH3 

5. Anthocyanins are responsible for the red, purple and blue colors of many flowers, fruits  and vegetables. In an acidic solution, anthocyanins have structure A, below, and in a  basic solution structure B.

HO

OH

O

R

OH

R

OH

OH

HO

OH

+

O

R

OH

R

OH

Basic solution A

Acidic solution B

One form is colored and the other form is colorless. Which form (A or B)  would you expect to be colored? 3 pts. 

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (15 total points)

Give the symmetry (symmetric or antisymmetric) of the indicated molecular orbitals  

6.

of the following conjugated systems:

b) c)

a)

3 pts.

3 pts. 3 pts.

HOMO of the ground state

LUMO of the ground state HOMO of the excited state

Will the stereochemistry of the methyl groups be cis or trans in the product of the  

7.

following electrocyclic reaction?

(Wavy lines mean  stereochemistry  

unspecified) C 

C

H CH3 

H CH3 

answer

CH3 CH3 3 pts.

8. Will the following suprafacial cycloaddition occur thermally (Δ) or photochemically?

+

O O

N CH3 

O O

N

CH3 

3 pts.

answer (Δ or hυ)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(30 total points)

9. Draw the structure of the major organic product:

a) (3 pts.) (3 pts.) SO3H

HNO3 Zn, HCl

H2SO4,

b) (3 pts.) (3 pts.)

+

CH3 

CH3CH

AlBr3 

Br

KMnO4 

10. Draw an appropriate structure in each box: a)

Cl

NO2 

(3 pts.) (3 pts.)

NO2

b)

NaOCH3 

Carbanion Intermediate

(one resonance structure)

O

Major Nucleophilic  Substitution Product

NO2 

O 

N

(3 pts.) (3 pts.)

Br

CH2CH2CH3 

(NBS),  peroxide

Carbon Radical Intermediate (one resonance structure)

Major Organic Product

c) (3 pts.) O CH2CH3 

C

Br2 

FeBr3 

Carbocation Intermediate

(one resonance structure)

(3 pts.)

Major Electrophilic  

Substitution Product

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(7 total points)

11. Draw the structure (include all H’s in your drawing) of the organic intermediate in the following reaction.

(3 pts.) Br

NH2 

NH2 

NaNH2, NH3 

+

CH3 

organic intermediate

12. Outline the steps to complete the following synthesis:

(4 pts.)

Make: From: CH3 

and any other desired reagents

Br

CH2CH CH3

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (21 total points)  

1. Draw the structure of the following compounds:

a) 2,5-dimethyl-1,4-hexadiene

b) p-methylphenol

c) o-bromobenzoic acid

d) benzyl alcohol

e) m-nitroaniline

(3 pts. each, 6 points total).  

(3 pts.) (3 pts.) (3 pts.)

(3 pts.) (3 pts.)

2.

Encircle the two compounds which are expected to be aromatic according to Hückel’s Rule: H HH H

(-)

C

CH

H H

C

(+)

C

(-) (+)

C

C C

C C N

N

H H H H

H H

E

A B C D

CH2 CH CH CH CH CH2 

G

F

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (18 total points)  

3. Draw appropriate structures in the boxes:

CH3 

a)

CH3 

HBr

(3 pts.) (3 pts.)

two resonance structures of intermediate carbocation

HBr

(3 pts.) (3 pts.)

+

1,2 product 1,4 product

Which product of the above reaction (the 1,2 or the 1,4) will  

b)

be the major product under conditions of kinetic control?

Which product will be the major product under conditions  

c)

of thermodynamic control?

(3 pts.) (3 pts.)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(9 total points)  

4. Complete the following Diels-Alder reaction:

3 pts. 3 pts.

+

Diene Dienophile

O

C

C

CCN O

CH3 

5. Anthocyanins are responsible for the red, purple and blue colors of many flowers, fruits  and vegetables. In an acidic solution, anthocyanins have structure A, below, and in a  basic solution structure B.

R

OH

R

OH

+ OH 

HO

O

R

OH

HO

OH

O

R

OH

OH

Acidic solution

Basic solution

A B

One form is colored and the other form is colorless. Which form (A or B)  would you expect to be colored? 3 pts. 

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (15 total points)  

Give the symmetry (symmetric or antisymmetric) of the indicated molecular orbitals  

6.

of the following conjugated systems:

a) b) c)

3 pts. 3 pts. 3 pts.

LUMO of the excited state HOMO of the ground state HOMO of the excited state

Will the stereochemistry of the methyl groups be cis or trans in the product of the  

7.

following electrocyclic reaction?

(Wavy lines mean  

stereochemistry  

unspecified) C 

C

H CH3 

H CH3 

answer

CH CH3 3 3 pts.

8. Will the following suprafacial cycloaddition occur thermally (Δ) or photochemically (hυ)?

+

O O

O

O O

O

3 pts.

answer (Δ or hυ)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(30 total points)  

9. Draw the structure of the major organic product:

a) (3 pts.) (3 pts.) SO3H

b)

+

HNO3 

H2SO4,

CH3 

CH3CHBr

(3 pts.)

AlBr3 

Zn, HCl (3 pts.)

KMnO4 

10. Draw an appropriate structure in each box:

a) (3 pts.) O CH2CH3 

C

Br2 

FeBr3 

Carbocation Intermediate

(one resonance structure)

(3 pts.)

Major Electrophilic  

Substitution Product

b)

Cl

NO2 

c)

NO2 

NaOCH3 

Carbanion Intermediate

(one resonance structure)

O

(3 pts.) (3 pts.)

Major Nucleophilic  

Substitution Product

NO2 

O 

N

(3 pts.) (3 pts.)

Br

CH2CH2CH3 

(NBS),  peroxide

Carbon Radical Intermediate (one resonance structure)

Major Organic Product

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(7 total points)

11. Draw the structure (include all H’s in your drawing) of the organic intermediate in the following reaction.

(3 pts.) Br

NH2 

NH2

NaNH2, NH3 

+

CH3 

organic intermediate

12. Outline the steps to complete the following synthesis:

CH2CH2CH2CH3 

Make: From: Cl

(4 pts.)

and any other desired reagents

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (21 total points)

1. Draw the structure of the following compounds:

a) 4-methyl-1,3-pentadiene

b) p-isopropylphenol

c) o-nitrobenzoic acid

d) benzaldehyde

e) p-bromoaniline

(3 pts. each, 6 points total).  

(3 pts.) (3 pts.) (3 pts.)

(3 pts.) (3 pts.)

2.

Encircle the two compounds which are expected to be aromatic according to Hückel’s Rule: H

H(-)

H

C

C

(-) (+) (-) CH

H H C

C C N

N

H H

H H

E

A B C D H(-)

CH2 CH CH CH CH CH2 

G

F

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (18 total points)

3. Draw appropriate structures in the boxes: a)

CH3

CH3 HBr

(3 pts.) (3 pts.)

two resonance structures of intermediate carbocation

HBr

(3 pts.) (3 pts.)

+

1,2 product 1,4 product

Which product of the above reaction (the 1,2 or the 1,4) will  

b)

be the major product under conditions of kinetic control?

Which product will be the major product under conditions  

c)

of thermodynamic control?

(3 pts.) (3 pts.)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(9 total points)

4. Complete the following Diels-Alder reaction:

3 pts. 3 pts.

+

Diene Dienophile

O

C

C OCH3 

CC O

OCH3

5. Anthocyanins are responsible for the red, purple and blue colors of many flowers, fruits  and vegetables. In an acidic solution, anthocyanins have structure A, below, and in a  basic solution structure B.

R

OH

R

OH

+ OH 

HO

O

R

OH

HO

OH

O

R

OH

OH

Acidic solution

Basic solution

A B

One form is colored and the other form is colorless. Which form (A or B)  would you expect to be colored? 3 pts. 

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (15 total points)

Give the symmetry (symmetric or antisymmetric) of the indicated molecular orbitals  

6.

of the following conjugated systems:

a) b) c)

3 pts. 3 pts. 3 pts.

LUMO of the ground state HOMO of the excited state HOMO of the ground state

Will the stereochemistry of the methyl groups be cis or trans in the product of the  

7.

following electrocyclic reaction?

(Wavy lines mean  stereochemistry  

unspecified) C 

C

H CH3 

H CH3 

answer

CH3 CH3 3 pts.

8. Will the following suprafacial cycloaddition occur thermally (Δ) or photochemically?

+

O O

N CH3 

O O

N

CH3

3 pts.

answer (Δ or hυ)

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(30 total points)

9. Draw the structure of the major organic product:

a) (3 pts.) (3 pts.)

+

CH3 

CH3CH

AlBr3 

Br

KMnO4 

b) (3 pts.) (3 pts.) SO3H

HNO3 

H2SO4,

10. Draw an appropriate structure in each box:

Zn, HCl

a)

NO2 

O O 

N

(3 pts.) (3 pts.)

Br

CH2CH2CH3 

(NBS),  peroxide

Carbon Radical Intermediate (one resonance structure)

Major Organic Product

b) (3 pts.) O CH2CH3 

C

Br2 

FeBr3 

Carbocation Intermediate

(one resonance structure)

(3 pts.)

Major Electrophilic  

Substitution Product

c)

Cl

NO2 

NO2 

NaOCH3 

Carbanion Intermediate

(one resonance structure)

(3 pts.) (3 pts.)

Major Nucleophilic  

Substitution Product

Copyright, 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(7 total points)

11. Draw the structure (include all H’s in your drawing) of the organic intermediate in the following reaction.

(3 pts.) Br

NH2 

NH2 

NaNH2, NH3 

+

CH3 

organic intermediate

12. Outline the steps to complete the following synthesis:

(4 pts.)

Make: From: CH3 

and any other desired reagents

Br

CH2CH CH3

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (2 pts. each, 20 total points)

1. Draw the structure of the following:

a) 3-methyl-2-butanol

2 pts. 2 pts.

b)

2-ethylbutanal

2 pts.

e)

c) 3-phenyl-2-pentanone d) ethylene oxide

the hydrazone of acetone f) 2-methoxybutane

2 pts. 2 pts. 2 pts.

g) acetaldehyde2 pts. h) isopropyl alcohol2 pts. 

2 pts.

i) 2-methylcyclohexanone

j) t-butyl methyl ether 2 pts.

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (4 pts. each, 27 total points)

2. Draw the structure of the major organic product:

a)

CH3 

CH3 C CH3 

CH2OH

CrO3,

H2O, H2SO4 

(3 pts.)

b)

CH2CH2OH

CrO3 

HCl pyridine(3 pts.) (PCC)

c)

CH3 

O

1) LiAlH4 

(excess)

(3 pts.)

d)

HC C CH3 

O

OH

2) H3O+ 

(3 pts.)

C 1) LiAlH4 

(excess)

2) H3O+ OEt EtOH +

e)1) NaBH4 

(3 pts.)

CH3 

O

H

f)

CH3CH2CH C O

2) H3O+ 

(3 pts.)

CH3CH2C

CH2CH3NH2 

1) NH2 

H2SO4 

g)

OH

2)

, KOH

(3 pts.)

H2SO4, CH3 C CH2CH3 

CH3 

OH

E1 

h) PBr3 

(3 pts.)

i)

CH3 

CH3 

OH

C CH3 H

1) CH3

2) NaBr

(SN2)

(SN2)

O

S Cl

O 

show stereochemistry show stereochemistry

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (8 points total)

3. Which reaction, A or B, is the better Williamson Synthesis of the indicated ether?

ONa

+ A) 

CH2Br

B)

Br

+

CH2ONa

Answer

(2 pts.)

CH2 O

4. Encircle the side favored at equilibrium for the following acid-base reaction:

ONa

+ CH3CH2ONa

(2 pts.)

OH

+ CH3CH2OH

5. Draw structures in the boxes to complete the following Grignard Synthesis using a protecting group: O

Br

CH2CH2 OH OH

1)

Mg

C

H

+

CH2CH2 OH OH

H+ 

2)

HC

OH

C

O H

(2 pts.)

3)

CH2 O

H3O+ (2 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 24 points total)

6. Draw the structure of the major organic product:

a)

b)

c)

O

CH2C

CH

O

OCH3 +

CH2 

CH2MgBr

(excess)

Hg(OAc) 1) 2 

CH3CH2OH

NaBH4 2)

H3O++ CH3OH

(3 pts.) (3 pts.)

(3 pts.)

d) e)

CH2 C

O

CH2 C CH3 

CH2CH3 CH2CH3 

CH2CH3 CH2CH3 O

1) NaOCH2CH3 2) H3O+ 

CH3CH2OH

H2SO4 

1) CH3MgCl

(3 pts.) (3 pts.)

C CH2 CH3

O

2) H3O+ 

f) (3 pts.) NaCN

H2SO4 

CH3 CH3 

g) h)

O

CH3CH2CH2C

O

H

(CH3)2NH H2SO4 

CH3NH2 

H2SO4 

(3 pts.) (3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 21 total points)

7. Draw structures in the boxes to complete the following syntheses:

a) A Grignard Synthesis: 

(3 pts.)

(3 pts.)

Mg

CH3 

CH

CH3 

OH

CH CH

CH3 CH3 

an organic halide

b) A Wittig Synthesis: a primary organic halide

a Grignard reagent

(3 pts.)

O3P

1)

2) H3O+ 

(3 pts.)

BuLi

(3 pts.) (3 pts.)

CH3 

CH

CH3 

CH C

CH3 

CH2CH3 

A Wittig reagent

A carbonyl compound

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (2 pts. each, 20 total points)

1. Draw the structure of the following:

a) 2-ethoxypentane2 pts. 

2 pts.

b) 2-ethylcyclopentanone

c) acetone2 pts. d) t-butyl alcohol2 pts. e) ethyl methyl ether 2 pts. 

2 pts.

f) 3-ethyl-3-pentanol

g) ethylene oxide2 pts.2 pts.

h)

2-methylbutanal

2 pts.

2 pts.

j)

i) 4-phenyl-2-butanone the hydrazone of acetaldehyde

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (4 pts. each, 27 total points)

2. Draw the structure of the major organic product:

O

a)

1) NH2 

(3 pts.)

NH2 

b)

OH

2)

H2SO4 , KOH

(3 pts.)

H2SO4, CH3CH2 C

CH3 

CH3 

OH

E1 

c) PBr3 

(3 pts.)

CH3CH2 C H

CH3 

OH

(SN2) O

show stereochemistry

d)

e)

CH3 

CH3 

1) CH3

2) NaBr (SN2)

OH

(3 pts.)

(3 pts.)

CrO3,

S Cl

O 

show stereochemistry

CH2CH2 

H2O, H2SO4 

f)

CH3 O (excess) 

1) LiAlH4 

(3 pts.)

g)

CH C OH O

2) H3O+ 

(3 pts.)

CH3CH2CH2C 1) LiAlH4 

(excess)

h)

OEt EtOH +

2) H3O+ 

CrO3 HCl pyridine(3 pts.) CH3 

CH3 C CH3

CH2OH

O

(PCC)

i)

1) NaBH4 

2) H3O+ 

CH2C H

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (8 points total)

3. Encircle the side favored at equilibrium for the following acid-base reaction:

OH

CH2ONa

+

ONa

(2 pts.)

CH2OH +

4. Which reaction, A or B, is the better Williamson Synthesis of the indicated ether? ONa

A) +

CH3CH2CH2Br

B)

CH3CH2CH2ONa

+

CH3 Br

CH3 

CH3CH2CH2 O

CH3 

Answer

(2 pts.)

5. Draw structures in the boxes to complete the following Grignard Synthesis using a protecting group:

Br

C

O H

CH2CH2 OH OH H+ 

(2 pts.)

1)

2)

Mg

OH O

CH3CH2 CH C H +

CH2OH

CH2OH

3)

H3O+ (2 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 24 points total)

6. Draw the structure of the major organic product:

a)

MgBr

(3 pts.)

O

CH2CH2C OEt

H3O+ 

+ + CH3OH

(excess)

b) c)

CH

O

CH2 

Hg(OAc) 1) 2 CH3OH

NaBH4 2)

(3 pts.) (3 pts.)

d) e)

CH2 C

O

CH2 C CH3 

CH2CH3 CH2CH3 

CH2CH3 CH2CH3 O

1) NaOCH3 2) H3O+ 

CH3OH

H2SO4 

MgBr

1)

(3 pts.) (3 pts.)

C CH2 CH3 

O

2) H3O+ 

f) (3 pts.) 

g) h)

C CH3 

O

C CH3 

O

H

NaCN

H2SO4 

(CH3)2NH H2SO4 

(3 pts.)

CH2CH2C (3 pts.) CH3CH2NH2 

H2SO4 

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 21 total points)

7. Draw structures in the boxes to complete the following syntheses:

a) A Wittig Synthesis: 

(3 pts.)

(3 pts.)

O3P

a primary organic halide

BuLi

(3 pts.)

CH3C

CH3 

CHCH2CH CH3 

A Wittig reagent

A carbonyl compound

(3 pts.)

b) A Grignard Synthesis: (3 pts.)

(3 pts.)

CH3 

CH3 

MgCH3CH2CH CH CHCH2CH3 OH

(3 pts.)

an organic halide

1)

a Grignard reagent

2) H3O+ 

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (2 pts. each, 20 total points)

1. Draw the structure of the following:

a) 2-methoxybutane

b) acetaldehyde

c) isopropyl alcohol

d) 2-methylcyclohexanone

e) t-butyl methyl ether

f) 3-methyl-2-butanol

2 pts. 2 pts. 2 pts. 2 pts. 2 pts. 2 pts. 2 pts.

g)

2-ethylbutanal

2 pts.

h) 3-phenyl-2-pentanone i) ethylene oxide

j) the hydrazone of acetone

2 pts. 2 pts.

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (4 pts. each, 27 total points)

2. Draw the structure of the major organic product:

a)

CH3 

CH3 

1) CH3

2) NaBr (SN2)

O

S Cl O

(3 pts.)

OH show stereochemistry

OH

b) PBr3 

(3 pts.)

c)

C CH3 

H

O

(SN2)

(excess)

show stereochemistry

(3 pts.)

C 1) LiAlH4 

OEt EtOH +

2) H3O+ 

d)1) NaBH4 

(3 pts.)

CH3 

O

H

e)

CH3CH2CH C O

2) H3O+ 

(3 pts.)

CH3CH2C

CH2CH3NH2 

1) NH2 

H2SO4 

OH

2)

, KOH

f) (3 pts.) H2SO4, CH3 C

CH2CH3 

g)

CH3 CH3 

E1 

(3 pts.)

CH3 C CH3 

CH2OH

CrO3,

H2O, H2SO4 

h)

CH3 

O

1) LiAlH4 

(excess)

(3 pts.)

HC C CH3 

OH

2) H3O+ 

CH2CH2OHHCl pyridine(3 pts.) 

i)

CrO3 

(PCC)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(8 points total)

3. Draw structures in the boxes to complete the following Grignard Synthesis using a protecting group: O

Br

CH2CH2 OH OH

1)

Mg

C

H

+

CH2CH2 OH OH

H+ 

2)

HC

OH

C

O H

(2 pts.)

3)

CH2 O

H3O+ (2 pts.)

4. Which reaction, A or B, is the better Williamson Synthesis of the indicated ether?

ONa

+ A) 

CH2Br

B)

Br

+

CH2ONa

Answer

(2 pts.)

CH2 O

5. Encircle the side favored at equilibrium for the following acid-base reaction:

ONa

+ CH3CH2ONa

(2 pts.)

OH

+ CH3CH2OH

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  

(3 pts. each, 24 points total)

6. Draw the structure of the major organic product:

O

a) (3 pts.) NaCN

H2SO4 

CH3 CH3 

b) c)

O

CH3CH2CH2C

O

H

(CH3)2NH H2SO4 

CH3NH2 

H2SO4 

(3 pts.) (3 pts.)

d)

O (3 pts.) CH3 

1) CH3MgCl

e)

C CH2 CH3

O

2) H3O+ 

CH2MgBr

f) g)

CH2C

CH

O

OCH3 +

CH2 

(excess)

Hg(OAc) 1) 2 

CH3CH2OH

NaBH4 2)

H3O++ CH3OH

(3 pts.) (3 pts.)

(3 pts.)

h)

CH2 C

O

CH2 C

CH2CH3 CH2CH3 

CH2CH3 CH2CH3 

1) NaOCH2CH3 2) H3O+ 

CH3CH2OH

H2SO4 

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 21 total points)

7. Draw structures in the boxes to complete the following syntheses: a) A Wittig Synthesis: 

(3 pts.)

O3P

a primary organic halide

(3 pts.)

BuLi

(3 pts.)

CH3 

CH

CH3 

CH C

CH3 

CH2CH3 

A Wittig reagent

A carbonyl compound

(3 pts.)

b) A Grignard Synthesis: (3 pts.)

Mg

(3 pts.)

CH3 

CH

CH3 

OH

CH CH

CH3 CH3 

an organic halide

a Grignard reagent

1)

2) H3O+ 

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (2 pts. each, 20 total points)

1. Draw the structure of the following:

a) 3-ethyl-3-pentanol

2 pts. 2 pts.

b)

2-methylbutanal

2 pts.

e)

c) 4-phenyl-2-butanone d) ethylene oxide

the hydrazone of acetaldehyde f) 2-ethoxypentane

2 pts. 2 pts. 2 pts.

g) acetone2 pts. h) t-butyl alcohol2 pts. 

2 pts.

i) 2-ethylcyclopentanone

j) ethyl methyl ether 2 pts.

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (4 pts. each, 27 total points)

2. Draw the structure of the major organic product:

a)

(3 pts.)

OH

CH2CH2 

CrO3,

H2O, H2SO4 

b)

CH3 

CH3 C CH3 

CH2OH

CrO3 

HCl pyridine(3 pts.) (PCC)

c)

CH3 O (excess) 

1) LiAlH4 

(3 pts.)

d)

CH C OH O

2) H3O+ 

(3 pts.)

CH3CH2CH2C 1) LiAlH4 

(excess)

e) f)

OEt EtOH + 2) H3O+ 

O

CH2C H

1) NaBH4 

2) H3O+ 

O

(3 pts.) (3 pts.)

1) NH2 

NH2 

g)

OH

2)

H2SO4 , KOH

(3 pts.)

H2SO4, CH3CH2 C

CH3 

CH3 

OH

E1 

h) PBr3 

(3 pts.)

CH3CH2 C H

CH3 

OH

(SN2) O

show stereochemistry

i)

CH3 

CH3 

1) CH3

2) NaBr (SN2)

S Cl O 

show stereochemistry

(3 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (8 points total)

3. Which reaction, A or B, is the better Williamson Synthesis of the indicated ether? ONa

A) +

CH3CH2CH2Br

B)

CH3CH2CH2ONa

+

CH3 Br

CH3 

CH3CH2CH2 O

CH3 

Answer

(2 pts.)

4. Encircle the side favored at equilibrium for the following acid-base reaction:

OH

CH2ONa

+

(2 pts.)

ONa

CH2OH

+

5. Draw structures in the boxes to complete the following Grignard Synthesis using a protecting group:

Br

C

O H

CH2CH2 OH OH H+ 

(2 pts.)

1)

2)

Mg

OH O

CH3CH2 CH C H +

CH2OH

CH2OH

3)

H3O+ (2 pts.)

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 24 points total)

6. Draw the structure of the major organic product:

a)

MgBr

(3 pts.)

O

CH2CH2C OEt

H3O+ 

+ + CH3OH

(excess)

b) c)

CH

O

CH2 

Hg(OAc) 1) 2 CH3OH

NaBH4 2)

(3 pts.) (3 pts.)

d) e)

CH2 C

O

CH2 C CH3 

CH2CH3 CH2CH3 

CH2CH3 CH2CH3 O

1) NaOCH3 2) H3O+ 

CH3OH

H2SO4 

MgBr

1)

(3 pts.) (3 pts.)

C CH2 CH3 

O

2) H3O+ 

f) (3 pts.) 

g) h)

C CH3 

O

C CH3 

O

H

NaCN

H2SO4 

(CH3)2NH H2SO4 

(3 pts.)

CH2CH2C (3 pts.) CH3CH2NH2 

H2SO4 

Copyright 2015, Professor Michael Rathke.

No part of this Exam may be reproduced or transmitted without written permission.  (3 pts. each, 21 total points)

7. Draw structures in the boxes to complete the following syntheses: a) A Grignard Synthesis: 

(3 pts.)

(3 pts.)

CH3 

CH3 

Mg

an organic halide

b) A Wittig Synthesis: 

a Grignard reagent

1)

2) H3O+ 

CH3CH2CH CH CHCH2CH3 OH

(3 pts.)

(3 pts.)

O3P

a primary organic halide

(3 pts.)

BuLi

(3 pts.)

CH3C

CH3 

CHCH2CH CH3 

A Wittig reagent

A carbonyl compound

(3 pts.)