Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (x) D2, Pd/C.
(h)
1208
views
Ch. 9 - Alkenes II: Oxidation and Reduction
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
Not the one you use?Change textbookSelect a different textbook
Table of contents
- Ch. 2 - General Chemistry Translated: Finding the Electrons114
- Ch. 3 - Alkanes and Cycloalkanes: Properties and Conformational Analysis109
- Ch. 4 - Acids and Bases: Electron Flow144
- Ch. 5 - Chemical Reaction Analysis: Thermodynamics and Kinetics118
- Ch. 6 - Stereoisomerism: Arrangement of Atoms in Space112
- Ch. 7 - Principles of Green (Organic) Chemistry3
- Ch. 8 - Alkenes I: Properties and Electrophilic Additions158
- Ch. 9 - Alkenes II: Oxidation and Reduction150
- Ch. 10 - Alkynes: Electrophilic Addition and Redox Reactions101
- Ch. 11 - Properties and Synthesis of Alkyl Halides: Radical Reactions108
- Ch. 12 - Substitution and Elimination: Reactions of Haloalkanes172
- Ch. 13 - Alcohols, Ethers and Related Compounds: Substitution and Elimination239
- Ch. 14 - Structural Identification I: Infrared Spectroscopy and Mass Spectrometry54
- Ch. 15 - Structural Identification II: Nuclear Magnetic Resonance Spectroscopy93
- Ch. 16 - Metals in Organic Chemistry48
- Ch. 17 - Carbonyl Addition Reactions: Aldehydes and Ketones45
- Ch. 18 - Nucleophilic Acyl Substitution I: Carboxylic Acids18
- Ch. 19 - Nucleophilic Acyl Substitution II: Carboxylic Acid Derivatives39
- Ch. 20 - Enolates: Carbonyl Addition and Substitution13
- Ch. 21 - Conjugated Systems I: Stability and Addition Reactions56
- Ch. 22 - Conjugated Systems II: Pericyclic Reactions54
- Ch. 23 - Benzene I: Aromatic Stability and Substitution Reactions64
- Ch. 24 - Benzene II: Reactions Influenced by the Aromatic Ring62
- Ch. 25 - Amines: Structure, Reactions, and Synthesis27
- Ch. 26 - Amino Acids, Proteins, and Peptide Synthesis9
- Ch. 27 - Carbohydrates, Nucleic Acids, and Lipids54
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471Not the one you use?Change textbook
Chapter 8, Problem 45h(ii)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ii) Cl2
(h) 
Verified step by step guidance1
Identify the type of reaction: The reaction involves an alkene and Cl₂, which is a halogenation reaction. In this reaction, the π-bond of the alkene reacts with Cl₂ to form a vicinal dihalide (two halogen atoms added to adjacent carbons).
Understand the mechanism: The reaction proceeds via an electrophilic addition mechanism. The π-electrons of the alkene attack one of the chlorine atoms, forming a cyclic chloronium ion intermediate.
Determine the regioselectivity and stereochemistry: The cyclic chloronium ion intermediate is opened by the attack of the chloride ion (Cl⁻) on the more substituted carbon, if applicable. This results in anti-addition, meaning the two chlorine atoms will be added to opposite sides of the double bond.
Draw the product(s): Replace the double bond in the alkene with single bonds and add one chlorine atom to each of the two carbons that were part of the double bond. Ensure the stereochemistry reflects anti-addition (if stereocenters are formed).
Verify the product(s): Check the structure of the product(s) to ensure that the addition of Cl₂ follows the anti-addition pattern and that the correct number of chlorine atoms has been added to the molecule.
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.
Electrophilic Addition
Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes. In the case of alkenes reacting with Cl₂, the double bond acts as a nucleophile, attacking the chlorine molecule, leading to the formation of a cyclic chloronium ion intermediate. This process is crucial for understanding how alkenes can undergo transformations to form more complex products.
Recommended video:
Guided course
09:23
1,2 vs 1,4 Addition
Stereochemistry
Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. When alkenes react with Cl₂, the addition can lead to the formation of stereoisomers, such as enantiomers or diastereomers, depending on the configuration of the resulting product. Understanding stereochemistry is essential for predicting the specific products formed during the reaction.
Recommended video:
1:38Polymer Stereochemistry Concept 1
Halogenation of Alkenes
Halogenation of alkenes is a specific type of electrophilic addition reaction where halogens, such as chlorine or bromine, add across the double bond of an alkene. This reaction typically results in the formation of vicinal dihalides, where two halogen atoms are added to adjacent carbon atoms. Recognizing the mechanism and outcome of halogenation is vital for predicting the products of the reaction with Cl₂.
Recommended video:
Guided course
03:45Halogenation Mechanism
Related Practice
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (i) Br2
(h)
1328
views
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vi) 1. OsO4 2. NaHSO3
(h)
1295
views
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (ix) H2, Pd/C;
(h)
1169
views
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl2, CH3OH
(h)
1128
views
Textbook Question
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H2SO4, H2O
(h)
1054
views