Textbook Question
The following reaction steps are shown using conventional electron pushing. (b) Use the bouncing arrow formalism to illustrate the formation of only the product shown.
(c)
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Ch. 8 - Alkenes I: Properties and Electrophilic Additions
Mullins1st EditionOrganic Chemistry: A Learner Centered ApproachISBN: 9780137566471
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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
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Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 22b
Mullins 1st EditionCh. 8 - Alkenes I: Properties and Electrophilic AdditionsProblem 22bChapter 7, Problem 22b
Suggest an alkene that, upon reaction with the appropriate hydrohalic acid, will produce only the alkyl halide shown. [Ignore stereochemistry.]
(b) 
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Identify the structure of the alkyl halide product. Determine the carbon skeleton and the position of the halogen atom in the alkyl halide.
Consider the mechanism of hydrohalic acid addition to alkenes. The reaction typically follows Markovnikov's rule, where the halogen adds to the more substituted carbon.
Determine the possible alkene structures that could lead to the given alkyl halide. The alkene should have a double bond positioned such that, upon addition of the hydrohalic acid, the halogen ends up on the correct carbon as per the product structure.
Select the alkene that, when reacted with the hydrohalic acid, will follow Markovnikov's rule and produce the desired alkyl halide. Ensure that the alkene structure matches the carbon skeleton of the product.
Verify that the chosen alkene will not lead to any other major products. Consider the stability of the carbocation intermediate formed during the reaction to ensure that the reaction proceeds as expected.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Markovnikov's Rule
Markovnikov's Rule states that in the addition of HX (hydrohalic acid) to an alkene, the hydrogen atom will attach to the carbon with more hydrogen atoms, and the halide will attach to the carbon with fewer hydrogen atoms. This rule helps predict the major product of the reaction, ensuring the halide ends up on the more substituted carbon.
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The 18 and 16 Electron Rule
Carbocation Stability
Carbocation stability is crucial in determining the outcome of alkene reactions with hydrohalic acids. More substituted carbocations (tertiary > secondary > primary) are more stable due to hyperconjugation and inductive effects. The formation of the most stable carbocation intermediate guides the regioselectivity of the reaction, influencing the final product.
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05:58Determining Carbocation Stability
Alkene Structure
The structure of the alkene determines the possible carbocation intermediates and the final product distribution. Identifying the correct alkene involves understanding its substitution pattern, which affects the regioselectivity of the addition reaction. The alkene must be chosen such that it leads to the exclusive formation of the desired alkyl halide upon reaction with the hydrohalic acid.
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1:59Alkene Metathesis Concept 5
Related Practice
Textbook Question
Suggest an alkene that, upon reaction with the appropriate hydrohalic acid, will produce only the alkyl halide shown. [Ignore stereochemistry.]
(d)
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Textbook Question
Which is the most likely transition state for the reactions shown? Explain your answer. [Note the difference in the size of the partial charges or partial unpaired electrons.]
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Textbook Question
The following reaction steps are shown using conventional electron pushing. (a) Draw the second product whose formation would have been rationalized with this same arrow.
(c)
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Textbook Question
A wayward chemist proposed the following mechanism for the addition of HBr to an alkene.
(a) Why is this mechanism unlikely?
(b) Compare the reaction coordinate diagrams for the actual mechanism studied in Section 8.3.1 and this alternate mechanism on the same graph.
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Textbook Question
Provide an arrow-pushing mechanism that rationalizes the formation of each alkyl halide in Assessment 8.19.
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