Textbook Question
For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.
(c)
621
views
14. Synthetic Techniques
Retrosynthesis
3:34 minutesProblem 50f
Textbook Question
Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.
(f) 
Verified step by step guidance1
Step 1: Analyze the starting material, 1,2-dimethylcyclohexene. It is a cyclohexene ring with two methyl groups attached at the 1 and 2 positions. The double bond is located between carbons 1 and 2.
Step 2: Identify the target compound. The structure provided shows a cyclohexane ring with two double bonds, making it a conjugated diene. The double bonds are located between carbons 1-2 and 3-4.
Step 3: To synthesize the conjugated diene, perform a dehydrogenation reaction. This involves removing hydrogen atoms from the cyclohexene ring to form the second double bond. A suitable reagent for this step is a strong base such as potassium tert-butoxide (KOtBu) or a catalytic dehydrogenation process.
Step 4: Ensure that the reaction conditions favor the formation of the conjugated diene. Conjugated systems are thermodynamically stable due to delocalization of π-electrons. Heat may be applied to drive the reaction toward the formation of the conjugated product.
Step 5: Verify the stereochemistry and ensure that the product is a racemic mixture if chirality is involved. Since the target compound does not show stereochemical indicators, focus on achieving the correct connectivity and conjugation in the final product.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
Video duration:
3mWas this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Electrophilic Addition Reactions
Electrophilic addition reactions are fundamental in organic chemistry, particularly for alkenes like 1,2-dimethylcyclohexene. In these reactions, an electrophile reacts with the electron-rich double bond of the alkene, leading to the formation of a more stable carbocation intermediate. This process is crucial for synthesizing various compounds, as it allows for the introduction of new functional groups into the molecule.
Recommended video:
Guided course
05:39
Features of Addition Mechanisms.
Stereochemistry
Stereochemistry is the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the context of synthesizing compounds from 1,2-dimethylcyclohexene, understanding stereochemistry is essential, especially when dealing with chiral products. The formation of stereoisomers can occur during reactions, and recognizing these configurations is vital for predicting the properties and reactivity of the resulting compounds.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Rearrangement Reactions
Rearrangement reactions involve the structural reorganization of a molecule, often leading to more stable products. In the synthesis of compounds from 1,2-dimethylcyclohexene, rearrangements can occur after electrophilic addition, where the initial carbocation may shift to form a more stable carbocation. This concept is important for understanding how to manipulate reaction pathways to achieve desired products in organic synthesis.
Recommended video:
Guided course
06:28Definition of Cope Rearrangement
Related Videos
Related Practice