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Organic Chemistry II (CHE 322) Final Spring 2020

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Sandra Watson
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draw the organic product for the following acid-catalyzed hydrolysis reaction. 

Stony Brook University

Organic Chemistry II (CHE 322)

CHE 322 Final Exam
This is a 110 minute exam. Make sure that you save your work regularly when using OscerSketch and submit answers regularly in case
you have an internet interruption.
This is an “open book’ exam, which means that you can use any web page or text. However, you must complete the exam on your own
without communication or assistance from any other person.
Oscer’s Honor Code
You must complete this exam without assistance from any other person and use no more than the allocated 110 minutes.
When you reach the end of the exam you should type your name in the answer box if you have followed these instructions.
Question 1
( 5 points )
Choose the order that has the following pentadienyl cations correctly arranged with respect to increasing stability.

Question 2
( 5 points )
A student was asked to draw out the mechanism for the following acid catalyzed nitrile hydrolysis reaction. Which intermediate should
not appear in the student’s mechanism?

Question 3
( 5 points )
Ruff degradation of D-aldohexose X does not give the same D-aldopentose as Ruff degradation of D-mannose. Give the name of the
D-aldohexose X. It cannot be D-mannose.

Question 4
( 5 points )
Five of the six structure shown below are terpenes. One of them is not. Choose the one that is not a terpene.

Question 5
( 5 points )
Draw the structure of the main product of the following reaction sequence.

Question 6
( 5 points )
Provide the major product(s) of this reaction. You must show stereochemistry using wedged and dashed bonds where appropriate.

Question 7
( 5 points )
Provide the major product for the following sequence of reactions.

Question 8
( 5 points )
The following reaction will undergo back to back aldol condensations. Draw the product.

Question 9
( 5 points )
Draw the reactant of the following intramolecular Diels-Alder reaction.

Question 10
( 5 points )
Draw the thermodynamic product of the following reaction that utilizes deuterium labeled hydrochloric acid.

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Organic Chemistry II (CHE 322) Final Spring 2020

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