Multiple Choice
Predict the major organic product of the following reaction.
1
views
10. Addition Reactions
Halohydrin
4:47 minutesProblem 66b
Textbook Question
What is the major product of each of the following reactions?
b. 
Verified step by step guidance1
Step 1: Analyze the structure of the reactant. The molecule is a substituted cyclohexene with a double bond. The reaction involves bromine (Br₂) in methanol (CH₃OH), which suggests a bromination reaction in the presence of a nucleophile (methanol).
Step 2: Understand the mechanism. Bromine reacts with the double bond via electrophilic addition. The π-electrons of the double bond attack Br₂, forming a bromonium ion intermediate.
Step 3: Consider the role of methanol. Methanol acts as a nucleophile and will attack the more substituted carbon of the bromonium ion due to steric and electronic factors, leading to regioselectivity.
Step 4: Predict the stereochemistry. The attack by methanol occurs from the opposite side of the bromonium ion (anti-addition), resulting in a trans product.
Step 5: Draw the major product. The major product will have a bromine atom and a methoxy group (-OCH₃) added across the double bond in an anti configuration, with the methoxy group on the more substituted carbon.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
Video duration:
4mKey Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition Reactions
Electrophilic addition reactions involve the addition of an electrophile to a nucleophile, typically across a double bond. In the case of alkenes, such as cyclohexene, the π bond acts as a nucleophile, reacting with electrophiles like Br2. This reaction leads to the formation of a more stable product, often resulting in the addition of halogens across the double bond.
Recommended video:
Guided course
05:39
Features of Addition Mechanisms.
Regioselectivity
Regioselectivity refers to the preference of a chemical reaction to yield one structural isomer over others when multiple possibilities exist. In the bromination of cyclohexene, the regioselectivity is influenced by the stability of the carbocation intermediates formed during the reaction. Understanding which carbon atoms are more favorable for electrophilic attack is crucial for predicting the major product.
Recommended video:
Guided course
05:09Heck Reaction
Solvent Effects
The choice of solvent can significantly influence the outcome of a chemical reaction. In this case, methanol (CH3OH) serves as a polar protic solvent, which can stabilize charged intermediates and facilitate the reaction. The solvent can also participate in the reaction, potentially leading to the formation of products that include methanol-derived groups, such as methoxy groups, in the final product.
Recommended video:
Guided course
01:16Identification of polarity in solvents
Related Videos
Related Practice