Skip to main content
Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins - Organic Chemistry: A Learner Centered Approach 1st Edition
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
All textbooksMullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 61b(iv)
Chapter 7, Problem 61b(iv)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H2SO4 , H2O
(b) Structural representation of alkenes for predicting products of acid-catalyzed hydration reactions.

Verified step by step guidance
1
Step 1: Identify the type of reaction. The given reagents, H₂SO₄ (sulfuric acid) and H₂O (water), indicate an acid-catalyzed hydration reaction. This reaction typically adds a hydroxyl group (-OH) to the alkene, converting it into an alcohol.
Step 2: Determine the regioselectivity of the reaction. Acid-catalyzed hydration follows Markovnikov's rule, meaning the -OH group will add to the more substituted carbon of the double bond, while the hydrogen (H) will add to the less substituted carbon.
Step 3: Analyze the structure of the alkene. Locate the double bond in the molecule and identify the two carbons involved in the double bond. Determine which carbon is more substituted (has more alkyl groups attached) and which is less substituted.
Step 4: Consider carbocation stability. During the reaction mechanism, a carbocation intermediate is formed. The reaction will favor the formation of the most stable carbocation (tertiary > secondary > primary). If necessary, rearrangements may occur to achieve a more stable carbocation.
Step 5: Write the product structure. After the addition of H and -OH groups according to Markovnikov's rule, draw the final product, ensuring the hydroxyl group is attached to the more substituted carbon and the hydrogen is attached to the less 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:
1m
Was this helpful?

Key Concepts

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

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the presence of strong acids like H₂SO₄, the alkene's double bond acts as a nucleophile, attacking the electrophilic hydrogen, leading to the formation of a carbocation intermediate. This step is crucial for predicting the products of reactions involving alkenes.
Recommended video:
Guided course
09:23
1,2 vs 1,4 Addition

Carbocation Stability

Carbocation stability is a key concept in organic reactions, as the stability of the carbocation intermediate influences the reaction pathway and product distribution. Carbocations can be classified as primary, secondary, or tertiary, with tertiary carbocations being the most stable due to hyperconjugation and inductive effects. Understanding the stability of these intermediates helps predict the major products formed during electrophilic addition reactions.
Recommended video:
Guided course
05:58
Determining Carbocation Stability

Hydration Reaction

The hydration reaction involves the addition of water (H₂O) to an alkene, typically facilitated by an acid catalyst like H₂SO₄. This reaction results in the formation of alcohols, where the hydroxyl group (-OH) is added to the more substituted carbon of the alkene, following Markovnikov's rule. Recognizing this principle is essential for predicting the final products when alkenes react with acids and water.
Recommended video:
Guided course
09:11
Alkyne Hydration
Related Practice
Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)2 , H2O 2. NaBH4

(b)

Textbook Question

Given the name, draw the structure of the following compounds.

(e) (3R,5S)-5-chloro-3-isopropylcycloheptene

Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (vi) 1. BH3 2. H2O2, NaOH

(b)

4
views
Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions:(ii) HCl;

(b)

1
views
Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iii) HBr, H2O2

(b)

1
views
Textbook Question

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (i) HBr;

(b)

3
views