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Exam 3 - Basic Organic Chemistry II - Spring 2004 - Prof. Clarke W. Earley, Exams of Organic Chemistry

A university exam from a basic organic chemistry ii course, held in spring 2004. The exam consists of 5 pages and covers various topics such as claisen condensation reactions, drawing missing organic products, enol forms, synthesis of diketoester, and more. Students are required to answer each question within the given time and space, and partial credit is given for incomplete responses.

Typology: Exams

Pre 2010

Uploaded on 08/01/2009

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Name:
CHEM 20482 - Basic Organic Chemistry II - Spring 2004
Exam #3 - 100 Points
Your examination should have a total of 5 pages. For each question, write your answer in the space provided. You have
1 hour to complete this exam, so use your time wisely. Do not waste time on questions that you find particularly difficult or
time-consuming before completing those questions that you can answer more rapidly. Partial credit is available for incomplete
responses, so it is worthwhile to attempt every question (if you have time).
1. [8 pts] Two of the following molecules undergo Claisen condensation reactions. Indicate which two molecules react
under Claisen condensation reaction conditions and draw the structure of the products of these two reactions.
CH3CH3
CH3
CH3
O
O
CC
CH3
CH3CH3
CH3
CC
O
O
CH3
CH3
CH3
CH3CH2
O
O
CC
2. [12 pts] Draw the structure of the missing organic product expected from each of the following chemical reactions.
CH2CH3
NaOCH2CH3
CH2C H3
1 ) OH
2 ) H3O+
CH2=CH−CH2Br
NaOCH2CH3 /
1 ) OH
2 ) H3O+
C
O
OO
O
C
A
heat
B
3) heat
C
1
pf3
pf4
pf5

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Name:

CHEM 20482 - Basic Organic Chemistry II - Spring 2004Exam #3 - 100 Points

1 hour to complete this exam, so use your time wisely. Do not waste time on questions that you find particularly difficult or^ Your examination should have a total of 5 pages. For each question, write your answer in the space provided. You have

time-consuming before completing those questions that you can answer more rapidly. Partial credit is available for incompleteresponses, so it is worthwhile to attempt every question (if you have time).

1. [8 pts] Two of the following molecules undergo Claisen condensation reactions. Indicate which two molecules reactunder Claisen condensation reaction conditions and draw the structure of the products of these two reactions.

CH 3 CH 3

CH 3 CH 3

O

C O C

CH 3

CH 3 CH 3

C C^ CH^3

O

O CH 3 CH^3 CH 3

CH 3 CH 2

O

C C O

2. [12 pts] Draw the structure of the missing organic product expected from each of the following chemical reactions.

CH 2 CH 3

NaOCH 2 CH 3 C H 2 C H 3

1 ) OH−

2 ) H 3 O+

CHNaOCH 2 =CH−^2 CHCH^32 B r/ 1 ) OH2 ) H − 3 O+

C

O

O OCO^ A

heat B

  1. heat C

3. [18 pts] Answer the following questions for the -diketoester shown below.

CH 2 CH 3

CH 3 CH 3

C C

O O

O

enol

(a) Draw one of the enol forms of this molecule.

(b) Show how this molecule can be synthesized using a Dieckmann cyclization.

(c) Show how this molecule can be synthesized from acylation of a ketone (ketone + ester).

(d) Describe appropriate reaction conditions for the following transformation.

CH 2 CH 3

CH 3 CH 3 CH 3 CH 3

C C CH 2 CH 3

O O

O C

O

(e) Predict the structure of primary organic product expected from the reaction:

-diketoester GGGNaOCHGGGGGGGGG^ GCHGGGGGA

CH =CH-CHO?

5. [16 pts] Draw the structure of the missing organic products in the following series of chemical reactions.

CH 2 CH^2 CH^3

−OCH 2 CH 3

CH 3 CH 2 CH 2 CH 2 B r

1 ) OH2 ) H −

3 O+

−OCH 2 CH 3

CH 3 B r

1 ) OH2 ) H − 3 O+

CH 3 CH 2

O O

C C O A

  1. heat B

  2. heat

O

C D

6. [6 pts] Draw three (3) isomers of C H  N that are all secondary (2 ) amines.

7. [6 pts] Rank each of the following compounds in order of decreasing basicity. (1=most basic, 5=most basic).

N

NH 2

CH 3 CH^3

O

C N

H CH CH NH  OH  (C H ) N

8. [10 pts] Use the curved arrow formalism to indicate the accepted mechanism for each of the following chemical reactions.

(a) 2CH^3 CH 2 CH^3

O

C O GGG2 NaOCHGGGGGGGGGGGGA

CH OH

(b)

CH 3 CH 2 CH 3

CH 3 NaOCH 3 CH 3 OH

O

O

C O^ O

+ C^ C