A compound that is 85.6 % C and 14.4 % H and has a molecular mass of 56.1 amu reacts with water

step 1 In this video, we're going to determine the identity of a hydrocarbon. We are given data that ca

A compound that is 85.6 % C and 14.4 % H and has a molecular...

A compound that is $85.6 \%$ C and $14.4 \% \mathrm{H}$ and has a molecular mass of $56.1$ amu reacts with water and sulfuric acid to produce a compound that reacts with acidic potassium dichromate solution to produce a ketone. What is the name of the original hydrocarbon?

Key Concepts

Oxidation of Secondary Alcohols to Ketones

This concept describes the chemical transformation where a secondary alcohol is converted into a ketone by removal of hydrogen. Mild oxidizing agents such as acidified potassium dichromate are typically employed to achieve this change without over-oxidizing the molecule.

Acid?Catalyzed Hydration of Alkenes

In the presence of an acid catalyst like sulfuric acid, alkenes undergo hydration—the addition of water—to form alcohols. The reaction proceeds via the formation of a carbocation intermediate and typically follows Markovnikov's rule, dictating the regiochemistry of the added –OH group.

Markovnikov's Rule

Markovnikov's rule is used to predict the outcome of addition reactions to unsymmetrical alkenes, stating that in the addition of a protic acid, the hydrogen atom bonds to the carbon with the greater number of hydrogen atoms, leading to the more stable carbocation intermediate and ultimately to a regioselectively substituted product.

Percent Composition and Molecular Formula Determination

This concept involves using the percentages of elements present and the overall molecular mass to deduce a compound's molecular formula. In organic chemistry, by calculating the molar amounts of each element, one can establish the stoichiometric ratio that defines the compound’s empirical and then molecular formula.

Alkenes and Unsaturation

Alkenes are hydrocarbons characterized by at least one carbon–carbon double bond. This unsaturation not only defines their general formula but also results in distinct reactivity patterns, such as electrophilic addition reactions, that are foundational in organic synthesis.

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