Why does radical bromination with Br2 work cleanly on cyclohexane as shown here: Br2 Br hv But this substitution does not work nearly as well with cyclohexene? Br2 Br hv Cyclohexane will preferentially do an addition reaction, forming 1,2-dibromocyclohexane. Cyclohexene has allylic C-H bonds, which are more difficult to break. Radical bromination only works on six-membered rings. • Cyclohexene will preferentially do an addition reaction, forming 1,2-dibromocyclohexane.

Why does radical bromination with Br2 work cleanly on cyclohexane as shown here: Br2 Br hv But this substitution does not work nearly as well with cyclohexene? Br2 Br hv Cyclohexane will preferentially do an addition reaction, forming 1,2-dibromocyclohexane. Cyclohexene has allylic C-H bonds, which are more difficult to break. Radical bromination only works on six-membered rings. • Cyclohexene will preferentially do an addition reaction, forming 1,2-dibromocyclohexane.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter8: Addition Via Carbocation

Section: Chapter Questions

Problem 18CTQ: The reactants, intermediates, final products, and all curved arrows showing bonds forming...

See similar textbooks

Similar questions

The reactants, intermediates, final products, and all curved arrows showing bonds forming andbreaking are collectively referred to as the mechanism of a reaction. For the following reactants: a. Explain why the original statement of Markovnikov’s rule does not help in this case, but themodern restatement of Markovnikov’s rule tells you which carbon will get the X (Cl). b. Show the mechanism of the most likely addition reaction between the reactants.
Fill both dashes in the paragraph Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is: ---------.
1 example of reaction for each of the types of organic reactions: substitution, elimination, addition, and rearrangement. Show:a. the overall reaction (reactants --> products)b. the reaction mechanism (indicate intermediate product)c. indicate which is the reactive species or intermediate in the reaction (radical? electrophile? nucleophile?)d. overall description of the reaction eg., radical substitution or SR
Fill the blank space. Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound containing a phenol group with antioxidant properties is: ---------.
a. How many monochlorination products can be obtained from the radical chlorination of methylcyclohexane? Disregard stereoisomers.b. Which product would be obtained in greatest yield? Explain.c. How many monochlorination products would be obtained if all stereoisomers are included?
Complete the mechanism for the given conjugate addition reaction. Carefully follow the directions. CH3CH=CH−CO2CH3+NH2CH3⟶conjugate addition product
a) How many monochlorination products can be obtained from the radical chlorination of methylcyclohexane? Disregard stereoisomers. b) Which product would be obtained in greatest yield? Briefly explain. c) How many monochlorination products would be obtained if all stereoisomers are included?
In the presence of a radical initiator (Z•), tributyltin hydride (R3SnH, R = CH3CH2CH2CH2) reduces alkyl halides to alkanes: R′X + R3SnH → R′H + R3SnX. The mechanism consists of a radical chain process with an intermediate tin radical: This reaction has been employed in many radical cyclization reactions. Draw a stepwise mechanism for the following reaction.
Please circle the most stable radical in photo.
Draw a reaction-energy diagram for the propagation steps of the free-radical addition of HBr to isobutylene. Draw curves representing the reactions leading to both the Markovnikov and the anti-Markovnikov products. Compare the values of ∆G° and Ea for the rate-limiting steps, and explain why only one of these products is observed.
PLEASE HELP DRAW THE FREE RADICAL SUBSTITUTION OF CYCLOHEXANE WHICH INOLVES THE 3 STEPS WHICH ARE initiation , propagation and termination
1 example for organic rearrangement reaction show: a. the overall reaction (reactants --> products) b. the reaction mechanism (indicate intermediate product) c. indicate which is the reactive species or intermediate in the reaction (radical? electrophile? nucleophile?) d. overall description of the reaction eg., radical substitution or SR