Chapter 6 Carbocation Rearrangement Assignment The most common carbocation rearrangements are a hydride shift and a methyl shift. Another type of carbocation rearrangement is an alkyl shift, which is typically possible when a structure involves a small ring (with ring strain) and a carbocation that can be rearranged so that a more stable ring (5- or 6-membered) is formed. Draw the mechanism that would account for the following carbocation rearrangement. For full credit, you must also number the carbons in both structures to accurately indicate the bonding between each carbon. + +

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. OH CH3 + + H3C CH₂ CH3 First stage in synthesis of the preservative BHT • You do not have consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one. ▼ H3PO4 ? OH CH3 CH3 CH3 CH3

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Answer the question below the reaction. H3C H3C H3C OH H3C In the second step of the reaction mechanism, which of the following is formed? CH3 CH3 CH3 + Excess NH4Cl CH3 CH3 CH3 CH3 H₂SO4 CH3 CI ха +H2O

Answer the question below the reaction. O4S H3C H3C H3C OH In the first step of the reaction mechanism, which of the following is formed? CH3 H3C CH3 CH3 + Excess NH4Cl OH CH3 (+) -OH2 CH 3 CH3 OH CH3 H₂SO₁ CH3 CI ха +H2O

Draw the most stable resonance form for the intermediate in the following electrophilic substitution reaction. CI CI HNO3 / H2SO4 O2N You do not have to consider stereochemistry. • Include all valence lone pairs in your answer. • In cases where there is more than one answer, just draw one.

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Draw the rearrangement mechanism for the following image #10

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6) You have decided to repeat the reaction from Question 5 using a slightly different alkene starting material. You now observe 3 products, and you suspect that your major product (Product A) is the result of a carbocation rearrangement. Draw the mechanism for the formation of Product A and indicate which type of carbocation rearrangement has occurred. H₂O H₂SO4 A OH 67% Major Product B OH 32% Minor Product C 1% OH