Concept explainers
(a)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
(b)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
(c)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
(d)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
(e)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
(f)
Interpretation:
The rearranged structure of more stable carbocation has to be suggested.
Concept Introduction:
Stability order of carbocation:
A carbon containing three bonds with positive charge is known as carbocation. This cat ion is stabilized by rearranging charge within the molecule.
The stability order of the carbocation is
Trending nowThis is a popular solution!
Chapter 9 Solutions
Organic Chemistry
- Show how a 1,2-shift forms a more stable carbocation from each intermediate.arrow_forwardGiven that a primary carbocation is less stable than a tertiary carbocation, would you expect that a reaction that creates a primary carbocation would be more or less responsive to solvent polarity than a reaction that creates a tertiary carbocation, and why?arrow_forwardIdentify the carbocation which can rearrange via a 1,2-methyl shift.arrow_forward
- Construct an efficient three-step synthesis of 1,2-epoxycyclopentane from bromocyclopentane by dragging the appropriate formulas into the bins. Note that each bin will hold only one item, and not all of the given reagents or structures will be used.arrow_forwardWhich of the following carbocations is likely to undergo rearrangement through a methyl shift? A. I B. II C. III D. I and II E. II and IIIarrow_forwardTwo of the carbocations are prone to rearrangement. Show how they might rearrange to more stable carbocationsarrow_forward
- Consider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply? Substitution at a stereocenter gives predominantly a racemic productarrow_forwardDo hydration reactions like this one have Markovnikov and anti-Markovnikov products? I know that for addition of halides on alkene double bonds, there are Markovnikov products becasue of 1,2-halide/methyl shifts, but there usually aren't shifts in hydration reactions. Essentially, would the Markovnikov/major product for this reaction have a hydroxy group attached to the tertiary carbocation and the anti-Markovnikov/minor product for this reaction have a hydroxy group attached to the adjacent secondary carbocation?arrow_forward1, part A) In the reaction below, draw all of the possible products. 1, part B) For all the products you have drawn, draw their corresponding carbocations while also identifying if each is 1o/2o/3o carbocation. In addition, starting from alkene - provide complete accurate arrow-pushing mechanisms of each carbocation formation. 1, part C) In part B, circle the carbocation which is *most* stable, indicate why.arrow_forward
- Fill in the blank for this reaction by using the E1 mechanism that includes rearrangemntarrow_forwardWhen Br2 is added to buta-1,3-diene at -15 °C, the product mixture contains 60% ofproduct A and 40% of product B. When the same reaction takes place at 60 °C, theproduct ratio is 10% A and 90% B.If you had a solution of pure A, and its temperature were raised to 60 °C, what wouldyou expect to happen? Propose a mechanism to support your prediction.arrow_forwardCarbocations are carbons bearing a formal positive charge. a. Carbocations can be stabilized by induction and hyperconjugation. Explain each of these forms of stabilization.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning