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Ch. 6 - The Reactions of Alkenes • The Stereochemistry of Addition Reactions
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 6 - The Reactions of Alkenes • The Stereochemistry of Addition ReactionsProblem 70a(4)
Chapter 7, Problem 70a(4)

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.
4. Br2 in CH2Cl2

Verified step by step guidance
1
Identify the type of reaction: The reaction of alkenes (cis-2-butene and trans-2-butene) with Br₂ in CH₂Cl₂ is a halogenation reaction. This involves the addition of bromine across the double bond of the alkene to form a vicinal dibromide.
Understand the mechanism: The reaction proceeds via an anti-addition mechanism. This means that the two bromine atoms will add to opposite sides of the double bond, leading to stereochemical outcomes.
Analyze the starting materials: For cis-2-butene, the two substituents on the double bond are on the same side, while for trans-2-butene, the substituents are on opposite sides. This stereochemistry will influence the stereoisomers of the product.
Predict the products for cis-2-butene: When Br₂ adds to cis-2-butene, the anti-addition mechanism will result in the formation of a pair of enantiomers (stereoisomers) because the two bromine atoms add to opposite sides of the plane of the double bond.
Predict the products for trans-2-butene: When Br₂ adds to trans-2-butene, the anti-addition mechanism will result in a meso compound. This is because the molecule has a plane of symmetry after the addition of bromine, making it achiral.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Alkene Reactivity

Alkenes are unsaturated hydrocarbons that contain a carbon-carbon double bond, which makes them reactive. The double bond can undergo various reactions, including halogenation, where halogens like Br2 add across the double bond. Understanding the reactivity of alkenes is crucial for predicting the products formed in reactions with different reagents.
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Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the case of alkenes, the presence of different substituents around the double bond can lead to the formation of stereoisomers, such as cis and trans isomers. Recognizing how stereochemistry influences product formation is essential for accurately depicting the outcomes of reactions.
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Halogenation Mechanism

The halogenation of alkenes typically involves an electrophilic addition mechanism, where the alkene reacts with a halogen molecule, resulting in the formation of a cyclic halonium ion intermediate. This intermediate can lead to the formation of vicinal dihalides, which may exist as stereoisomers depending on the configuration of the starting alkene. Understanding this mechanism is key to predicting the products and their stereochemical outcomes.
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Related Practice
Textbook Question

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

3. a peroxyacid

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Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

5. Br2 + H2O

b. With which reagents do the two alkenes react to form different products?

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Textbook Question

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

1. HCl

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Textbook Question

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

7. H2O + H2SO4

b. With which reagents do the two alkenes react to form different products?

1
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Textbook Question

Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

2. BH3/THF, followed by HO-, H2O2, H2O

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Textbook Question

1-Methylcyclohexene forms two products when it reacts with bromine in methanol.

a. Draw the mechanism for the formation of the products.

b. Describe their stereochemical relationship—that is, are they enantiomers or diastereomers?

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