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Chapter 4: Problem 186

Preparation and reactions of alcohols Alcohols can by prepared from alkyl halides, epoxides, alkenes, etc. When treated with acid, \(\mathrm{C}-\mathrm{OH}\) bond is cleaved heterolytically to form a carbocation which could then undergo substitution, elimination or rearrangement depending on the conditions and stability of the carbocation. When 1,2 -dimethyl cyclohexene is treated with cold dilute alkaline \(\mathrm{KMnO}_{4}\), the product obtained is

Short Answer

Expert verified
Based on the given reaction, 1,2-dimethyl cyclohexene reacts with cold dilute alkaline KMnO4. This results in the oxidative cleavage of the alkene (double bond) via a dihydroxylation process. The final product formed is 1,2-dimethylcyclohexane-1,2-diol.

Step by step solution

01

1. Identify reactants and reaction conditions

In this reaction, we have 1,2-dimethyl cyclohexene as the reactant and cold dilute alkaline \(\mathrm{KMnO}_{4}\) as the reagent.
02

2. Find the mechanism of reaction

Cold dilute alkaline \(\mathrm{KMnO}_{4}\) is a strong oxidizing agent that is commonly used for the oxidative cleavage of alkenes (double bonds). In this case, the oxidizing agent reacts with the alkene and breaks the double bond. This process is called "dihydroxylation." The double bond will be cleaved to form two new \(\mathrm{C}-\mathrm{OH}\) bonds on the adjacent carbons where the double bond was initially present.
03

3. Determine the product

In the reaction of 1,2-dimethyl cyclohexene with cold dilute alkaline \(\mathrm{KMnO}_{4}\), dihydroxylation of the double bond occurs. This results in the formation of two new \(\mathrm{C}-\mathrm{OH}\) bonds where the double bond initially was, along with the retention of the two methyl groups present in the parent compound. The final product formed is 1,2-dimethylcyclohexane-1,2-diol.

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Most popular questions from this chapter

Chlorobenzene is less reactive than benzyl chloride towards nucleophilic substitution because (a) the carbon of \(\mathrm{C}-\mathrm{Cl}\) bond in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) is sp \(^{2}\) hybridized and holds the electron pair more firmly as compared to sp \(^{3}\) carbon containing chlorine in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\). (b) the \(\mathrm{C}-\mathrm{Cl}\) bond in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) is less polar compared to that in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}\). (c) the C-Cl bond in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) acquires partial double bond character due to resonance involving the lone pair on chlorine atom. (d) the chlorine in \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{Cl}\) is deactivating due to its high electronegativity.

Meso - 2, 3-dibromobutane when heated with zinc dust in methanol gives mainly (a) cis but- 2 -ene (b) trans-but-2-ene (c) 1,3 -butadiene (d) 2 -bromobut- 2 -ene

If 4 -bromo-1-butanol is treated with sodium, a product of molecular formula \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\) is formed. Arrive at the structure and propose a mechanism.

Directions: Each question contains Statement- 1 and Statement-2 and has the following choices (a), (b), (c) and (d), out of which ONLY ONE is correct. (a) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for Statement-1 (b) Statement- 1 is True, Statement- 2 is True; Statement- 2 is NOT a correct explanation for Statement-1 (c) Statement- 1 is True, Statement- 2 is False (d) Statement- 1 is False, Statement- 2 is True Statement 1 Nucleophilicity does not always match with basicity. and Statement 2 While nucleophilicity is more related to size, polarizability and steric factors, the basicity is the ability to abstract a proton from a substrate.

Which of the following reactions will give benzyl chloride? (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{HCHO}+\mathrm{HCl} \stackrel{\mathrm{ZnCl}_{3}}{\longrightarrow}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{Cl}_{2} \stackrel{\mathrm{hv}}{\Delta}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{SO}_{2} \mathrm{Cl}_{2} \stackrel{\text { peroxide }}{\longrightarrow}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5}-\mathrm{CH}_{3}+\mathrm{SOCl}_{2} \rightarrow\)
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