The dehydration of 4-methylcyclohexanol yields only one product, 4-methylcyclohexene. --Ron Actually, at least three different isomers of methyl cyclohexene are produced. 1 methyl cyclohexene, 3-methyl cyclohexene and 4-methyl cyclohexene. It is a fascinating reaction undergoing a lot of recent study. It is becoming the classic example of the "Evelyn Effect" wherin the proportions of different products of a reaction vary with time as a result of the fact that the rates of the processes generating the different products differ in themselves. See http://ochemonline.pbwiki.com/f/Dehydration_Blog.doc for more information. - GM
4-methylcyclohexanol is an alcohol.
water
4-methylcyclohexanol can be dehydrated by heating it with a strong acid catalyst, such as sulfuric acid. The acid protonates the hydroxyl group, making it a better leaving group. This leads to the elimination of water molecule and formation of 4-methylcyclohexene.
The major product is 1-methylcyclohexene, formed by dehydration of 1-methylcyclohexanol. The minor product may include other isomeric forms of 1-methylcyclohexene or byproducts due to further dehydration or rearrangement reactions.
4-methylcyclohexanol can be dehydrated to form 4-methylcyclohexene using concentrated sulfuric acid as a catalyst. The reaction can be represented by the following chemical equation: 4-methylcyclohexanol → 4-methylcyclohexene + H2O
2-methylcyclohexanol---> 1-methylcyclohexene+ 3-methylcyclohexene + methylenecyclohexane 1-methylcyclohexene is the main product favored due to its more substituted double bond, followed by 3-methylcyclohexene and then methylenecyclohexane
4-methylcyclohexanol is soluble in hexane because it is a nonpolar molecule, similar to hexane. Nonpolar solutes tend to be soluble in nonpolar solvents like hexane due to similar intermolecular forces.
Protonation of the hydroxyl group on 4-methylcyclohexanol by phosphoric acid to form a good leaving group. Formation of a carbocation intermediate by loss of water molecule. Rearrangement of the carbocation to a more stable product (such as the alkene 4-methylcyclohexene). Deprotonation of the carbocation intermediate to yield the final dehydrated product.
Because 2- methylcyclohexanol is a secondary alcohol (2 R- groups) and can be oxidized to a ketone quite easity whereas 1- methylcyclohexanol is a tertiary alcohol (3 R- groups) and is not easily oxidized. Tertiary alcohols in general are very difficult to oxidize.
C7H14O is the formula for the compound.
4-methylcyclohexene, 3-methylcyclohexene and 1-methylcyclohexene which is the major product because it is trisubstituted as opposed to the first two which are only disubstituted
1. Add Al2O3 at 400 deg C to eliminate the -OH and form 1-methylcyclohexene 2. Add BH3 in THF, then H2O2 in OH- to add an -OH group to the less substituted carbon of the alkene mentioned above (hydroboration-oxidation is anti-Markovnikoff) 3. Add PCC in CH2Cl2 to form your ketone. I think. Came across this question myself and this is how i solved it. Not 100% sure if its correct though