Interpretation:
Given that the isobutyl cation spontaneously rearranges to the tert-butyl cation by a hydride shit. The nature of the rearrangement exergonic or endergonic is to be stated. Applying Hammond postulate, how the transition state for the hydride shift might look like is to be drawn.
Concept introduction:
The stabilities of the carbocations are in the order tertiary > secondary > primary. The conversion of a less stable system in to a more stable system will take place readily and it will be an exergonic process. According to Hammond postulate, the transition state of an exergonic reaction will resemble the structure of the reactants.
To state:
Whether the spontaneous rearrangement of isobutyl cation to the tert-butyl cation by a hydride shit is exergonic or endergonic.Further to draw, by applying Hammond postulate, the transition state for the hydride shift.
Trending nowThis is a popular solution!
Chapter 7 Solutions
Organic Chemistry
- The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium. a. What would be the major product if the NIH shift occurs? b. What would be the major product if the carbocation forms phenol by losing H+ or D+, rather than by going through the NIH shift?arrow_forwardName the kind of sigmatropic rearrangement that occurs in the following reaction.arrow_forward-Draw the transition state showing the allowed homo and lumo interaction of the mechanism -Draw the transition state showing the forbidden Homo/Lumo interaction for the mechanismarrow_forward
- subunits D,E,F help pleasearrow_forwardThis reaction is also an important reaction of the tricarboxylic acid cycle in cells, wherein the reaction occurs in neutral solution, so the acid groups are both ionized to the carboxylate form. The reaction is catalyzed by the stereospecific enzyme fumarase that utilizes only the trans form of 2-butenedioate ion (also known as fumarate) and produces only the (S)-2-hydroxysuccinate enantiomer (also known as (S)-malate). Draw the correct stereochemical structures of these two compounds of the fumarase-catalyzed reaction. Be sure to include all hydrogen atoms and show the carboxylates as anions.arrow_forward22. Which of the following statements is incorrect? Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the product in an endothermic reaction. Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the reactants in an exothermic reaction. The presence of more electron-donating alkyl groups ineffectively delocalize the positive charge in an organic molecule, making it less stable. The dehydration of primary alcohol proceeds via E2 mechanism. All of the abovearrow_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