When 3,3-dimethyl-1-butene is treated with HBr alone, the major product is 2-bromo-2,3-dimethylbutane. When the samealkene is treated with HBr and peroxide, the sole product is 1-bromo-3,3-dimethylbutane. Explain these results by referringto the mechanisms.

To find: The mechanism for the given reaction.

Answered: When 3,3-dimethyl-1-butene is treated…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 34MP: Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2Nâ‰¡C, along with the...

See similar textbooks

Similar questions

The reaction of (2S)-2-chloro-3-methylpentane with sodium iodide yields two products: (2R)-2-iodo-3-methylpentane and racemic 3-iodo-2-methylpentane. Account for the formation of each of these two products. For each product, you should show how it is formed and what that tells you about the mechanism of that specific reaction.
Reaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2Nâ‰¡C, along with the nitrile CH3CH2Nâ‰¡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.
On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-l-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.
When 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two productsare formed. Propose a mechanism that accounts for both of these products
2,3-Dimethylbutane reacts with bromine in the presence of light to give a mono brominated product. The further reaction gives a good yield of a dibrominated product. Predict the structures of these products, and propose a mechanism for the formation of the mono brominated product.
Reaction of but-1-ene with HBr gives two products in unequal amounts. In each case, identify the two products, state which is the major product, explain why it is the major product and give the mechanism for its formation.
When cyclohexene is treated with bromine in saturated aqueous sodium chloride, a mixture of trans-2-bromocyclohexanol and trans-1-bromo-2-chlorocyclohexane results.Propose a mechanism to account for these two products.
Treating 1-methyl-1-vinylcyclopentane with HCl gives mainly 1-chloro-1,2-dimethylcyclohexane. Propose a mechanism for the formation of this product.
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.
When 3-methyl-1-butene reacts with HBr, two alkyl halides are formed: 2-bromo-3-methylbutane and 2-bromo-2-methylbutane. Propose a mechanism that explains the formation of these two products.

Recommended textbooks for you

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305080485

Author:

John E. McMurry

Publisher:

Cengage Learning

Organic Chemistry

Chemistry

ISBN:

9781305580350

Author:

William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:

Cengage Learning

SEE MORE TEXTBOOKS

When 3,3-dimethyl-1-butene is treated with HBr alone, the major product is 2-bromo-2,3-dimethylbutane. When the same alkene is treated with HBr and peroxide, the sole product is 1-bromo-3,3-dimethylbutane. Explain these results by referring to the mechanisms.