What product are expected to obtain from reaction of 1-methylcyclohexanol with...?

Question

1. HBr
2. NaH
3. H2SO4
4. Na2Cr2O7

Answer 1

a) Bromization: R-OH + HBr → RBr + H2O
b) Deprotonation: R-OH + NaH → R-O-Na + H2
c) Dehydration producing 1-methylcyclohexene
d) Oxydation producing 1-methylcyclohexanone R=O

Answer 2

Lancenigo di Villorba (TV), Italy

ABOUT 1-METHYLCYCLOHEXANOL
This organic compound have a "chemical formula bruta" like C7H14O. As you understood, it is an ALCOHOL, more precisely a Tertiary Alcohol because the C1 placement's carbon atom binding the oxydril group binds also other three carbon atoms
(e.g. C2, C6's placements in the ring and the Methyl-Substituent Group attached to the ring in C1's placement).
The ALCOHOLS are Organic Compounds which may follows TWO MAIN CHEMICAL DESTINYs, e.g. "Elimination" and "N. Substitution".
ELIMINATION interests the conversion of Alcohol in Alkene or a related unsaturated hydrocarbon : you may think Alcohols lose water forming Alkene. Usually, Alcohols undergo this
De-Hydratation forming some Alkenes instead a lonely one. Thermodynamics remarks suggest that ELIMINATION become the MAIN EVENTS when you operate increasing the temperature.
Kinetic remarks suggest that ELIMINATION's rate take favour by the strong acidic (and hot) mixture.
NUCLEOPHILIC SUBSTITUTION interests the conversion of Alcohol in Alkyl Derivatives, e.g. I think to Halides or some BenzenSulphonates : you may think Alcohols exchange its Oxydril group for another substituent as halogen ion.
Usually, Alcohols undergo this Substitution forming some Alkyl Derivatives instead a lonely one (see Structural Isomery).
This remark highlights that the reaction involves a particular intermediate, e.g. the "Carbocation", that is a positive electrical charged poliaggregated.
Thermodynamics remarks suggest that N. SUBSTITUTIONs become the MAIN EVENTS when you operate monitoring (against excesses) the temperature.
Kinetic remarks suggest that N. SUBSTITUTION's rate are very influenced by solvent's characteristics, mainly its polarity.

REACTANT 1)
HBr is a very polar compound, it is a very strong acid when in aqueous media. Simply, Oxydril group is replaced by one bromine atom : it forms 1-METHYLCYCLOHEXIL-BROMIDE.

C7H14O + HBr <---> C7H13Br + H2O

REACTANT 2)
NaH is a METAL-HYDRIDE, so it reacts with any "Protic" compound, that are the compound having one hydrogen atom bound to an Electronegative atom one (see Pauling's Electronegativity). Simply, the hydrogen atom placed on the Oxydril group is replaced by a sodium's one : it forms SODIUM's 1-METHYLCYCLOHEXOXIDE and many HYDROGEN BUBBLEs(Danger!! Very explosive!!).

C7H14O + NaH <---> C7H13ONa + H2

REACTANT 3)
H2SO4 is a very polar compound, it have a VERY GREAT WATER-AFFINITY because in its concentrated solution it acts as De-Hydratating agent. As I precised, the REACTION GOES ONLY IF YOU USE CONCENTRATED H2SO4's SOLUTIONS.
When you warm the mixture, you obatin the related Alkenes, that are unsaturated hydrocarbons. The Alcohol loses its Oxydril group as Water, so it forms 1-METHYLCYCLOHEXENE.

C7H14O <---> C7H12 + H2O

REACTANT 4)
Na2Cr2O7 is a very polar compound, it is a very soluble salt while its aqueous solutions show a dark yellow hue. When you add concentrated H2SO4's solutions you note a darkening toward an orange hue : you formed CROMIC ACID, a strong oxidizer. The oxidizing action may interest several Alcohols, this one does not because it is a Tertiary Alcohol : I think nothing happens.

I hope this helps you.

Answer 3

1. 1-bromo-1-methylcyclohexane
2. the alkoxide of 1-methylcyclohexanol (with sodium as the counterion) and hydrogen gas
3. 1-methylcyclohexene
4. No reaction (1-methylcyclohexanol is a tertiary alcohol and thus you can't oxidize it to a cyclic ketone).

Answer 4

1-methylcyclohexanol