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7 Problems on Elements of Organic Chemistry II - Exam 2 | CH 232, Exams of Organic Chemistry

Material Type: Exam; Professor: Shaughnessy; Class: Elem Organic Chem II; Subject: CH-Chemistry; University: University of Alabama; Term: Spring 2009;

Typology: Exams

2009/2010

Uploaded on 02/25/2010

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Chemistry 232, Spring 2009
Dr. Shaughnessy
Exam #2
February 24th, 2009
Name: (print) CWID:
Honor Pledge: I promise or affirm that I will not at any time be involved with cheating,
plagiarism, fabrication, or misrepresentation while enrolled as a student at The University of
Alabama. I have read the Academic Honor Code, which explains disciplinary procedures that
will result from the aforementioned. I understand that violation of this code will result in
penalties as severe as indefinite suspension from the University.
_____________________________(signature)
You will have 1 hour and 30 minutes to complete this exam. When
time is called please stop all work and turn in your exam.
Show all work. Partial credit will be given where appropriate.
This exam has 9 pages. Make sure you have all 9 pages, and that they
are correctly copied, before starting the exam.
You may use molecular models to help you answer questions on this
exam.
You will not need a calculator or any other electronic device to complete
this exam.
Please put all cell phones (turn off or to silent), ipods, calculators, or
other electronic devices away in a book bag.
Your book and all notes should be placed out of sight of yourself and
your neighbors before the exam begins.
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Download 7 Problems on Elements of Organic Chemistry II - Exam 2 | CH 232 and more Exams Organic Chemistry in PDF only on Docsity!

Chemistry 232, Spring 2009

Dr. Shaughnessy

Exam

February 24th, 2009

Name: (print) CWID:

Honor Pledge : I promise or affirm that I will not at any time be involved with cheating,

plagiarism, fabrication, or misrepresentation while enrolled as a student at The University of

Alabama. I have read the Academic Honor Code, which explains disciplinary procedures that

will result from the aforementioned. I understand that violation of this code will result in

penalties as severe as indefinite suspension from the University.

_____________________________( signature )

You will have 1 hour and 30 minutes to complete this exam. When

time is called please stop all work and turn in your exam.

Show all work. Partial credit will be given where appropriate.

This exam has 9 pages. Make sure you have all 9 pages, and that they

are correctly copied, before starting the exam.

You may use molecular models to help you answer questions on this

exam.

You will not need a calculator or any other electronic device to complete

this exam.

Please put all cell phones (turn off or to silent), ipods, calculators, or

other electronic devices away in a book bag.

Your book and all notes should be placed out of sight of yourself and

your neighbors before the exam begins.

Problem Score

7 (12+ 5 bonus)

Total (100 + 5 bonus)

2. For each reaction below, provide the missing starting material(s), reagent(s), or product(s).

For reactions in which more than product can be formed, draw each major product. You

should not include products formed as minor products, however. You do not need to indicate

side products from the reagents used. Where necessary, clearly indicate the stereochemistry

of the products obtained. Note that some boxes may require more than one starting material

or reaction step (20 points)

O O

CH 3

O

HI

O

O

H 3 O+

  • Ph 3 PO a. b. c. d. e. 2 organic products

3. Tamoxifen is a drug used in the treatment of breast cancer. A possible synthesis of

tamoxifen starting from phenol is outlined below. Provide the missing structures and

reagents to complete the synthesis. (12 points)

OH

O

O

N(CH 3 ) 2

IR: 3400 cm-^1 (broad), 1680 cm-^1 C

A

B (C 13 H 10 O 2 )

2 ) H 3 O+

IR = 3400 cm-^1 (broad)

D (C 26 H 31 NO 2 )

POCl 3 pyridine O

(H 3 C) 2 N

Tamoxifen

5. Billy Joe is taking CH 232 for the fourth time. He has proposed the syntheses below.

Unfortunately for Billy Joe, there is a key flaw in each proposed reaction that would not

allow it to work. For each reaction, draw the major product that would actually be formed in

the box and propose an alternative way to make the desired molecule. (15 points)

O

O

OCH 3

1 ) LiAlH 4 2 ) H 3 O+

O

OH

O

1 ) CH 3 MgBr 2 ) H 3 O+^ CH^2 O 1 ) (^) MgBr 2 ) H 3 O+

O

a. b. c.

6. Treatment of nitroaromatic compound below with hydrogen and Pd provides an amine

intermediate ( A ), which is not isolated. Treatment of this intermediate with weak acid results

in cyclization to give 2-methyl-3,4-dihydroquinoline ( B ). Provide a detailed electron-

pushing mechanism for the converstion of A to B. You should show each step in the reaction

using arrows to show the electron flow. Be sure to indicate any atoms with formal charges in

your intermediates. (14 points)

NO 2

O

H 2 /Pd NH^2 O

H 3 O+^ N

+ H 2 O

A

not isolated

B