10 - Dehydration of 2-Methylcyclohexanol

10 - Dehydration of 2-Methylcyclohexanol - Dehydration of...

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Dehydration of 2-methylcyclohexanol Alcohol dehydration is an acid catalyzed reaction, which can be performed by strong, concentrated mineral acids such as sulfuric acid (H 2 SO 4 ) and phosphoric acid (H 3 PO 4 ).
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Background Alcohol dehydration proceeds by an elimination mechanism called E1 . minor product major product 1 st step - Protonation changes the very poor leaving group –OH into a good leaving group –OH 2 + . 2 nd step - Water departs, leaving behind a carbocation. This step is rate determining step (RDS) . 3 rd step - The base H 2 PO 4 - removes a proton from the carbon adjacent to the positively charged carbon, forming an alkene and regenerating the acid catalyst H 3 PO 4 . oxonium ion Saytzev’s rule : The more substituted alkene is the more stable product (major product).
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Dehydration of 2-methylcyclohexanol carbocation rearrangement major product bp 110° C minor products bp 165° C
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Experimental Procedure Changes from the Manual procedures: Use heating mantel instead of sand bath. Don't forget boiling chips.
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10 - Dehydration of 2-Methylcyclohexanol - Dehydration of...

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