Organic Chemistry : Help with Aldehyde and Ketone Synthesis
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Example Questions
Example Question #1 : Help With Aldehyde And Ketone Synthesis
What reagents are required to undergo Swern oxidation?
Pyridine, DMSO, and HCOOH
SOCl2, pyridine, and triethylamine
Dichloromethane, trimethylamine, and DMS
COCl2, triethylamine, and DMSO
Diethyl ether, organometallic compound, and H3O+
COCl2, triethylamine, and DMSO
Swern oxidation requires COCl2, triethylamine, and DMSO. The same reaction can be accomplished using PCC and dichloromethane. This reaction oxidizes an alcohol to a carbonyl, but only works with primary and secondary alcohols.
Example Question #1 : Carbonyl Products
Which of the following reactions will result in the given product?
A
D
E
B
C
C
The starting material first needs to be brominated, which occur at the tertiary carbon. Then, an elimination reaction needs to take place to form an alkene intermediate, which will transpire through the E2 pathway with the tertbutoxide ion in tertbutanol. After this, an alcohol needs to be formed through hydroboration because we need the carbonyl group on the less subsituted carbon. After an alcohol is formed, the PCC reaction can oxidize the alcohol to make it a carbonyl. All these reactions are shown in choice C.
Example Question #3 : Help With Aldehyde And Ketone Synthesis
A compound, 
What is the original compound?
1-chloro-1,2-dimethylcyclopentane
None of the other answers
2-chloro-1,1-dimethylcyclopentane
2-chloro-1,3-dimethylcylopentane
4-chloro-1,2-dimethylcyclopentane
2-chloro-1,3-dimethylcylopentane
In the first step of the reaction, a chlorine is abstracted and a double bond is formed. In the ozonolysis step, the molecule is broken at the double bond and each carbon at that bond gets double bonded to an oxygen. The presence of zinc keeps it from becoming a carboxylic acid.
Working backwards, you must remove the oxygens from the final product and redraw the molecule at the double bond. This intermediate is 1,3-dimethylcyclopentene. Next, the chlorine must be added to one of the carbons on the double bond. The only possible choice is 2-chloro-1,3-dimethylcyclopentane.
Example Question #2 : Carbonyl Products
Which of the following reagents is required to produce the ketone product?
In order to convert a secondary alcohol into a ketone, we must employ 
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