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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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BuyFindarrow_forward

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
Chapter 8.2, Problem 3P
Textbook Problem
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What product would you expect to obtain from addition of Cl2 to 1, 2-dimethyl- cyclohexene? Show the stereochemistry of the product.

Interpretation Introduction

Interpretation:

The product expected, along with its stereochemistry, from the addition of Cl2 to 1,2-dimethylcyclohexane is to be given.

Concept introduction:

The reaction of halogens to alkenes occurs with anti stereochemistry, that is, the two halogen atoms come from opposite faces of the double bond- one from top face and other from bottom face. In the first step the addition of halogen to the double bond in the alkenes results in the formation of a cyclic halonium ion with the simultaneous elimination of a halide ion. The larger halonium ion shields one side of the molecule. Hence the attack of the halide ion occurs from the opposite, unshielded side to yield the trans-product.

To give:

The product expected, along with its stereochemistry, when Cl2 is added to 1,2-dimethylcyclohexane.

Explanation of Solution

In the first step the addition of chlorine to the double bond in 1,2-dimethylcyclohexane results in the formation of a cyclic chloronium ion with the simultaneous elimination of a chloride ion...

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Chapter 8 Solutions

Organic Chemistry
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Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - What product would you obtain from catalytic...Ch. 8.7 - What product would you expect from reaction of...Ch. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - What products would you expect from reaction of...Ch. 8.8 - Propose structures for alkenes that yield the...Ch. 8.9 - What products would you expect from the following...Ch. 8.13 - What products are formed from acid-catalyzed...Ch. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Draw the structures of alkenes that would yield...Ch. 8.SE - The following alkene undergoes...Ch. 8.SE - From what alkene was the following 1, 2-diol made,...Ch. 8.SE - Predict the products for the following reactions,...Ch. 8.SE - Predict the products for the reactions in Problem...Ch. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - m-CPBA is not the only peroxyacid capable of...Ch. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Which of the reactions below would result in a...Ch. 8.SE - Reaction of 2-methylpropene with CH3OH in the...Ch. 8.SE - Iodine azide, IN3, adds to alkenes by an...Ch. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Treatment of 4-penten-l-ol with aqueous Br2 yields...Ch. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Predict the products of the following reactions...Ch. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Predict the products of the following reactions,...Ch. 8.SE - Which reaction would you expect to be faster,...Ch. 8.SE - What product will result from...Ch. 8.SE - The cis and trans isomers of 2-butene give...Ch. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Addition of HCl to 1-methoxycyclohexene yields...Ch. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - In planning the synthesis of one compound from...Ch. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Plexiglas, a clear plastic used to make many...Ch. 8.SE - Poly(vinyl pyrrolidone), prepared from...Ch. 8.SE - When a single alkene monomer, such as ethylene, is...Ch. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - An unknown hydrocarbon A with the formula C6H12...Ch. 8.SE - Using an oxidative cleavage reaction, explain how...Ch. 8.SE - Compound A, C10H18O, undergoes reaction with...Ch. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Simmons-Smith reaction of cyclohexene with...Ch. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Compound A has the formula C8H8. It reacts rapidly...Ch. 8.SE - How would you distinguish between the following...Ch. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Evidence that cleavage of 1, 2-diols by HIO4...Ch. 8.SE - Reaction of HBr with 3-methylcyclohexene yields a...Ch. 8.SE - We’ll see in the next chapter that alkynes...Ch. 8.SE - Hydroxylation of cis-2-butene with 0s04 yields a...Ch. 8.SE - Compound A, C11H16O, was found to be an optically...

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