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      • An adjacent bonding pair of electrons (i.e. a C-H bond) interacts with the empty p-orbital, and before you know it, the C-H bond has moved and a new, more stable carbocation has formed! The carbocation is then attacked by the nucleophile, giving a substitution reaction (S N 1) with rearrangement!
      www.masterorganicchemistry.com/2012/08/15/rearrangement-reactions-1-hydride-shifts/

      Rearrangement Reactions (1) - Master Organic Chemistry

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  3. chem.libretexts.org › Carbocation_RearrangementsCarbocation Rearrangements - Chemistry LibreTexts

    Jan 23, 2023 · Hydride shift now occurs when the hydrogen on the adjacent carbon formally switch places with the carbocation. The carbocation is now ready to be attacked by H 2 O to furnish an alkyloxonium ion because of stability and hyperconjugation.

  4. www.organicchemistrytutor.com › topic › carbocationsCarbocations: Stability and Rearrangements — Organic ...

    Instead of a hydrogen shift, the CH3 (methyl) group moves, transferring its electrons to the carbocation-bearing carbon. This shift transforms our structure. The original secondary carbocation becomes tertiary, offering a more stabilized structure.

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  6. chem.libretexts.org › Courses › Purdue9.2: 1,2-Shifts in Carbocations - Chemistry LibreTexts

    Which of the following carbocations are likely to undergo a shift? If a shift is likely, draw the new carbocation that would result.

  7. chem.libretexts.org › Bookshelves › Organic_Chemistry7.10: Rearrangements of the Carbocation and Sₙ1 Reactions

    Whenever reactants like alkyl halides form carbocations, the carbocations are subject to a phenomenon known as carbocation rearrangement. A carbocation is highly reactive and holds the positive charge on carbon with a sextet rather than an octet. There are two types of rearrangements: hydride shift and alkyl shift.

  8. www.masterorganicchemistry.com › 2012/08/15Rearrangement Reactions (1) - Master Organic Chemistry

    Aug 15, 2012 · One rearrangement pathway where an unstable carbocation can be transformed into a more stable carbocation is called a hydride shift. Look at the diagram below. In this reaction we have a secondary carbocation on the left hand side.

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  9. www.masterorganicchemistry.com › 2012/08/22Carbocation Rearrangement Reactions (2) – Alkyl Shifts

    Aug 22, 2012 · Alkyl shifts are most likely to occur when a quaternary carbon is adjacent to a secondary (or primary) carbocation. Alkyl shifts adjacent to strained rings (e.g. cyclobutane) can result in ring expansion. Table of Contents. Alkyl Shifts Can Lead To More Stable Carbocations, Too. The Mechanism Of Alkyl Shift Reactions.

  10. courses.lumenlearning.com › suny-potsdam-organic8.4. Carbocation rearrangements | Organic Chemistry 1: An ...

    Whenever an alkyl halide, alcohol or alkene is transformed into a carbocation, the carbocation may be subject to rearrangement. There are two types of carbocation rearrangements: a hydride shift and an alkyl shift.

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