Question

Write equations for the reactions of cis-2-butene with the following reagents, representing the reactants and products using structural formulas. (a) \(\mathrm{H}_{2} \mathrm{O}\) (b) HBr (c) \(\mathrm{Cl}_{2}\)

Short answer

(a) Forms butan-2-ol; (b) Forms 2-bromobutane; (c) Forms 2,3-dichlorobutane.

Step-by-step solution

Reaction with Water (Hydration)

Cis-2-butene reacts with water in the presence of an acid catalyst (usually sulfuric acid) to form an alcohol. The double bond in the cis-2-butene is broken, and a hydroxyl group (-OH) adds to one of the carbon atoms involved in the double bond, while a hydrogen atom adds to the other. This forms butan-2-ol as the major product. The reaction can be represented as:\[\text{cis-2-Butene} + \mathrm{H}_2\mathrm{O} \xrightarrow[]{\text{H}^+} \text{Butan-2-ol}\]Structural formula: \[\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_3 + \text{H}_2\text{O} \rightarrow \text{CH}_3-\text{CH}(\text{OH})-\text{CH}_2-\text{CH}_3\]

Reaction with Hydrogen Bromide (Hydrohalogenation)

Cis-2-butene reacts with HBr, where the double bond is broken, and a bromine atom (Br) adds to one of the carbons of the former double bond while a hydrogen atom adds to the other. According to Markovnikov's rule, bromide will attach to the more substituted carbon atom, producing 2-bromobutane as the product.Reaction equation:\[\text{cis-2-Butene} + \text{HBr} \rightarrow \text{2-Bromobutane}\]Structural formula: \[\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_3 + \text{HBr} \rightarrow \text{CH}_3-\text{CH}(\text{Br})-\text{CH}_2-\text{CH}_3\]

Reaction with Chlorine (Halogenation)

When cis-2-butene reacts with chlorine (\text{Cl}_2) in an inert solvent, the double bond is converted into a single bond, and each of the carbon atoms from the original double bond receives a chlorine atom. This leads to the formation of 2,3-dichlorobutane. Reaction equation:\[\text{cis-2-Butene} + \text{Cl}_2 \rightarrow \text{2,3-Dichlorobutane}\]Structural formula: \[\text{CH}_3-\text{CH}=\text{CH}-\text{CH}_3 + \text{Cl}_2 \rightarrow \text{CH}_3-\text{CH}(\text{Cl})-\text{CH}(\text{Cl})-\text{CH}_3\]

Key concepts

Hydration Reaction

Hydration reactions are a type of chemical reaction where water is added to an unsaturated compound, such as an alkene. In the case of cis-2-butene, hydration occurs in the presence of an acid catalyst, typically sulfuric acid, which helps in breaking the carbon-carbon double bond.

• During hydration, the alkene's double bond is converted into a single bond.
• This allows a hydroxyl group (-OH) from the water to bond with one of the carbon atoms.
• The hydrogen from water then attaches to the other carbon.

This process results in the formation of an alcohol, specifically butan-2-ol in the case of cis-2-butene. This reaction demonstrates how alkenes, like cis-2-butene, can be transformed into more complex molecules by introducing additional atoms, in this case from water.

Hydrohalogenation

Hydrohalogenation involves the addition of hydrogen halides, such as HBr, to alkenes. It's a common reaction for transforming alkenes into alkyl halides. For cis-2-butene, the hydrohalogenation process involves the breaking of the carbon-carbon double bond.

• The alkene double bond is broken and a hydrogen atom from HBr attaches to one carbon atom.
• The bromine atom attaches to the other carbon atom.

Following Markovnikov's rule, the bromine atom attaches preferentially to the more substituted carbon atom, which is the one with more carbon atoms already bonded to it. This results in the formation of 2-bromobutane. Hydrohalogenation is essential in producing a variety of alkyl halides from simple alkenes and follows predictable patterns based on the rule stated by Markovnikov.

Halogenation

Halogenation is a reaction in which a diatomic halogen molecule, such as chlorine, is added across the double bond of an alkene. This results in the saturation of the molecule, effectively breaking the double bond to form a dihaloalkane. When cis-2-butene undergoes halogenation with chlorine, the reaction proceeds as follows:

• The \( ext{Cl}_2\) molecule approaches the double bond, causing the bond to break.
• Each carbon from the previous double bond forms a new bond with a chlorine atom.

This leads to the formation of 2,3-dichlorobutane. The result is a fully saturated compound where both carbons of the original double bond now carry a chlorine atom. This type of reaction is straightforward and occurs readily, often used to introduce halogen atoms into organic compounds without complex side reactions.

Markovnikov's Rule

Markovnikov's rule provides a guideline that is vital in predicting the outcome of certain addition reactions, particularly those involving alkenes and asymmetrical reagents like HX, where X is a halogen. The rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen atoms, and the halogen (X) will bond with the carbon atom with fewer hydrogens or more substituents.

• This is used to predict the major product in hydrohalogenation reactions like with cis-2-butene and HBr.
• In this scenario, bromine becomes attached to the more substituted carbon in the former double bond.

Thus, cis-2-butene in the presence of HBr, according to Markovnikov's Rule, yields 2-bromobutane. Understanding this rule is crucial for anticipating the result of electrophilic addition reactions, leading to selective alkene transformations.

Alkene Reactivity

Alkenes are hydrocarbons characterized by having at least one carbon-carbon double bond, which significantly influences their chemical reactivity. This double bond is a region of high electron density, making alkenes highly reactive towards certain types of chemical reagents. Here are some characteristics of alkene reactivity:

• The double bond can act as a site for electrophilic addition reactions, where the alkene acts as a nucleophile, attacking electrophilic species.
• Alkenes like cis-2-butene readily undergo reactions such as hydration, hydrohalogenation, and halogenation.
• These reactions often result in the saturation of the double bond, converting it into a single bond and forming more complex molecules.

The reactivity of alkenes makes them valuable in organic synthesis as starting materials for a wide range of products. Understanding the influence of the double bond is critical to predicting and manipulating their chemical behavior.