Reducing agent question

[JoshuaSeid94]

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I am currently reviewing some organic chemistry for the DAT and have come across a problem regarding reducing agents. I am stuck on a reaction regarding the reducing agent PCC. The starting molecule is CH3CH2CH2CH2CH2OH (5 carbon alcohol) and it is reduced using PCC and CH2Cl. The answer I have down is CH2CH2CH2CH2CH2CHO (6 carbon aldehyde). This means that a 5 carbon alcohol was reduced into a 6 carbon aldehyde. This seems incorrect. Does the CH2Cl contribute another carbon to make it a 6 carbon molecule or is this answer incorrect? I would have thought that a 5 carbon alcohol would be reduced into a 5 carbon aldehyde when PCC and CH2Cl is used.

 

[DAT Destroyer]

I am currently reviewing some organic chemistry for the DAT and have come across a problem regarding reducing agents. I am stuck on a reaction regarding the reducing agent PCC. The starting molecule is CH3CH2CH2CH2CH2OH (5 carbon alcohol) and it is reduced using PCC and CH2Cl. The answer I have down is CH2CH2CH2CH2CH2CHO (6 carbon aldehyde). This means that a 5 carbon alcohol was reduced into a 6 carbon aldehyde. This seems incorrect. Does the CH2Cl contribute another carbon to make it a 6 carbon molecule or is this answer incorrect? I would have thought that a 5 carbon alcohol would be reduced into a 5 carbon aldehyde when PCC and CH2Cl is used.

Indeed. A 5 carbon primary alcohol is oxidized into a 5 carbon aldeyde when PCC oxidation is employed. . The carbon skeleton does NOT increase. The CH2Cl2 is merely the solvent.

Hope this helps..

Dr. Romano