Textbook Question
Predict the product(s) that would result when molecules (a)–(p) are allowed to react under the following conditions: (v) 1. TsCl, Et₃N 2. NaOt-Bu (vi) H₂SO₄ If no reaction occurs, write 'no reaction.'
(f)
8. Elimination Reactions
Cumulative Substitution/Elimination
Problem 41b
Textbook Question
Given the reactants shown, what type of elimination would you expect to occur?
(b) 
Verified step by step guidance1
Step 1: Analyze the structure of the reactants. The molecule on the left contains a cyclopentane ring with a chlorine atom attached to a carbon that is adjacent to a double bond. This is a secondary alkyl halide. The molecule on the right is tert-butanol, which is a bulky alcohol.
Step 2: Consider the reaction conditions. Tert-butanol is often used in elimination reactions, and its bulky nature suggests that steric hindrance will favor elimination over substitution. Additionally, the presence of a strong base (likely the alkoxide form of tert-butanol) will promote elimination.
Step 3: Determine the type of elimination mechanism. The bulky base and the secondary alkyl halide suggest that the reaction will proceed via an E2 mechanism. In an E2 reaction, the base abstracts a proton from a β-carbon, and the leaving group (chlorine) departs simultaneously, forming a double bond.
Step 4: Examine the stereochemistry of the elimination. For an E2 reaction, the β-hydrogen and the leaving group must be anti-periplanar (i.e., opposite and in the same plane). In this case, the chlorine atom and the β-hydrogen are positioned appropriately for anti-periplanar elimination.
Step 5: Predict the product. The elimination will result in the formation of a conjugated diene, as the double bond already present in the molecule will extend conjugation with the newly formed double bond. This increases the stability of the product.
Verified video answer for a similar problem:This video solution was recommended by our tutors as helpful for the problem above
Was this helpful?
Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Elimination Reactions
Elimination reactions involve the removal of atoms or groups from a molecule, resulting in the formation of a double bond or a ring structure. In organic chemistry, these reactions are typically classified as either E1 or E2 mechanisms, depending on the reaction conditions and the nature of the substrate. Understanding the type of elimination is crucial for predicting the products formed during the reaction.
Recommended video:
Guided course
00:40
Recognizing Elimination Reactions.
E2 Mechanism
The E2 mechanism is a concerted elimination process where a base abstracts a proton while a leaving group departs simultaneously, leading to the formation of a double bond. This mechanism is favored in strong bases and requires a specific geometric arrangement of the substrate, often involving anti-periplanar orientation of the leaving group and the hydrogen being removed. Recognizing the conditions that favor E2 is essential for predicting the outcome of the reaction.
Recommended video:
Guided course
09:36Drawing the E2 Mechanism.
Substituent Effects
The presence of substituents on a cyclohexene can significantly influence the type of elimination reaction that occurs. For instance, bulky groups can hinder certain pathways, while electron-withdrawing or donating groups can stabilize transition states or intermediates. Understanding how these substituents affect reactivity and selectivity is vital for predicting the products of elimination reactions.
Recommended video:
2:02Directing Effects in Substituted Pyrroles, Furans, and Thiophenes Concept 1
0:38mWatch next
Master Intro to Substitution/Elimination Problems with a bite sized video explanation from Johnny
Start learningRelated Videos
Related Practice