FINAL COPY -- MONDAY JULY 30, 2012

THE FOLLOWING IS INFORMATION THAT MAY BE USEFUL AS YOU PREPARE FOR
THE THIRD TEST IN ORGANIC CHEMISTRY II WHICH WILL BE GIVEN ON 
THURSDAY, AUGUST 2, 2012.

THE TEST HAS BEEN PREPARED AND COMMENTS ABOUT IT APPEAR AT THE END OF 
THIS MEMO.

The third test of the semester will cover material from chapter 15 on 
Electrophilic Aromatic Substitution (Table 15.2 will be given to you),
chapter 16 (aldehydes and ketones beginning at section 16.4), 
chapter 17 (carboxylic and their derivatives), and chapter 20 (amines) 
of the Solomon's textbook.  The test could have:

1. Nomenclature problems--carboxylic acids and their derivatives and 
amines. In the other sections of the test many compounds are identified 
by name and not structure.  You will need to know the names of many 
chemicals we saw during the entire course.

2. Reactions involving the preparation and use of aldehydes, ketones, 
carboxylic acids and their derivatives, and amines. Such questions may appear 
as reactions where you will have to show the necessary reagents to complete the 
reaction (mutiple steps may be necessary) or draw the structure of the major 
organic product. Many questions may include aromatic systems and 
electrophilic aromatic substitution reactions requiring the use of table 
15.2 which will be provided.

3. A mechanism which could involve hemiacetal/acetal formation or 
hydrolysis, or ester formation or hydrolysis.

4. A thought question on some topic I covered during the course.

5. Use of qualitative organic analysis.  For example, describe a
simple chemical test that would distinguish between acetone and 
propanal.

6. A preliminary list of SimOrg qualitative organic analysis tests you will 
need to know are as follows: solubility test (including 5% sodium 
bicarbonate test, 5% sodium hydroxide test, 5% hydrochloric acid test), 
bromine in carbon tetrachloride test, potassium permanganate test, 
chromic acid test, Tollen's test, 2,4-DNP test, Beilstein test.....

7. Words that you may need to define are as follows:
Chapter 16: hemiacetal, acetal, hydrazone, thioacetal, oxime, ylide, 
iodoform reaction.

Chapter 17: carboxyl group, acyl group,  nitrile, lactone, lactam, 
carboxylate ion, Fischer esterification

Chapter 20: primary, secondary or tertiary amine, quaternary ammonium salt, 
imine, enamine, arylamine, aminium ion, arenediazonium salt, reductive 
amination, sulfonamide, Hinsberg test, Sandmeyer reaction.

NOTES ABOUT TEST 3 (WHICH WILL BE 5 PAGES AND HAVE AN EXTENDED TIME 
ALLOWANCE):

1. (10 pts)There are 5 terms (from item 7 above) to define and give an 
exact example.
2. (24 pts) There are 8 names of organic substances where you will have to 
draw the structure of each.
3. (16 pts) There are 8 pairs of compounds for which you will have to name 
and describe a simple chemical test that would differentiate the 
compounds. See item 5 and 6 above.
4. (10 pts) You will have to draw a complete mechanism for a reaction 
mentioned in item 3 above.
5. (12 pts) There are 6 reactions where you will have to draw the 
structure of the major organic product.
6. (18 pts) There are 9 reactions showing a reagent and product for which
you will have to supply the missing reagents.  More than one step may be 
necessary and electrophilic aromatic substitution reactions may be used.
7. (10 pts) This question will test your ability to draw together concepts 
that I mentioned during the course.  


If you have any questions about the above, please send me an email message at 
bshine@ramapo.edu