Concept explainers
(a)
Interpretation: Based on Hammond’s postulate the greater selectivity for bromination Vs chlorination of an
Concept Introduction : Hammond’s postulate can be described as the transition state of reaction matches with the reactants or products and with its energy.
(b)
Interpretation: Based on Hammond postulate, the fact of the relative reactivity of C-H bonds of an alkane for free radical chain halogenation to be 3° > 2°> 1º needs to be explained.
Concept Introduction :
Hammond’s postulate can be described as the transition state of reaction matches with the reactants or products and with its energy.
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Experimental Organic Chemistry: A Miniscale & Microscale Approach (Cengage Learning Laboratory Series for Organic Chemistry)
- C=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forward2arrow_forwardBromine adds to cis- and trans-2-butene to give different diastereomers of 2,3-dibromo- butane. What does this say about the mode of addition of bromine to this alkene? H3C Br Bry H CH, Br `H. H,C Br Brg HH Br CH3arrow_forward
- Which represents an efficient synthetic route to go from an alkane to an alkene? O elimination with NaNH2, followed by a water workup O anti-Markovnikov hydrohalogenation, followed by elimination O radical bromination, followed by elimination O hydration, followed by elimination O hydration, followed by ozonolysis of the double bondarrow_forward4. A hydrocarbon with IHD of 2 showed a persisting yellow color in the bromine test. What is the likely identity of the compound? a bicyclic compound an alkene a benzene ring an alkyne a straight chain hydrocarbonarrow_forward1. Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, C6H13Br. On treatment of this alkyl halide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isometric with the starting alkene is formed. What is the structure of this hydrocarbon and how do you think it is formed from an alkyl bromide? 2. 1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-Octen-3-ol into a less effective molecule. Write a complete reaction equation for the hydrogenation of this alkenol.arrow_forward
- Cis-trans isomerism is possible for which of the following alkene/s? а. CH,=CH-CH,-CH,-CH3 b. CH;-CH=CH-CH,-CH3 CH;-CH=CH, CH,=CH-CH,-CH3 С. d.arrow_forwardWhat is the major product of the reaction between 2-methylbut-2-ene and Br2 in H2O?arrow_forward5. An unknown hydrocarbon A with the formula CóH12 reacts with 1 molar equivalent of H2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMNO4 in acidic solution, A gives two fragments. One fragment is propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are the structures of A, B, and C? Write all reactions and show your reasoning.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning