Sp2012 Org II Exam #2
Ch 18-19
(100 points)
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Answer all the questions.
1-10 are True / False. (20pts)
1)
Aldehydes and Ketones can undergo nucleophilic addition and
condensation reactions.
2)
Hoffman elimination reactions utilize a sterically demanding leaving
group.
3)
An ylide is an overall neutral molecule which contains two formal
charges of the same sign on adjacent atoms.
4)
Dimethylamine is more basic than ammonia.
5)
Three membered rings with one Nitrogen are called Arzoles.
6)
Clemmensen reduction converts ketones to Schiff bases.
7)
An isocyanate has the generic structure of RCNO
8)
Sandmeyer chemistry involves the reactions of diazonium salts with
Cobalt (I) salts.
9)
Protecting groups should be easy to put on, stable to the desired
reaction conditions, and then easily removed.
10)
Nitrogen inversion involves the N lone pair switching between an sp3
hybrid atomic orbital, and a 2p atomic orbital.
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11) Circle the most basic atom in the following species. (12pts)
12) Draw a Lewis structure including lone pairs for the following species:
(6pts)
Hydrogen Cyanide HCN
Methyldiazonium CH3N2+
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13) Give the reagents for the following transformations (12pts)
14) Name the following compounds in IUPAC acceptable terms. (9pts)
15) Draw a hemiacetal of an aldehyde. (3pts)
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16) Draw in all the curly arrows for the following mechanism of a
condensation reaction. (12pts)
17) What functional group is the product ? (2pts)
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18) Give the reagents for the following transformations. (12pts)
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19) For each pair of reactions (a-d), one reaction works better than
the other. Indicate which one works best, and write a single sentence to
explain why. (12pts)
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*Bonus question* (up to 5pts)
Indicate how you could convert cyclopentene into the following molecule.
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