Chapter 8 (ann).pptx - Chapter 8 Additions to alkenes...

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Chapter 8 Additions to alkenes
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Markovnikov-type Addition Reactions HX addition to alkenes to make Markovnikov alkyl halides Acid catalyzed hydration of alkenes Markovnikov alcohols Acid catalyzed addition of alcohols to alkenes to make Markovnikov ethers 2
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8.4 Electrophilic addition of HX to alkenes 3
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8.4 Electrophilic addition of HX to alkenes 4
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Mechanism of adding HX to alkene H + adds so as to make the most stable carbocation Halogen anion captures the carbocation Step 1 Step 2 5
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Mechanism of adding HX to alkene Hydrogen adds so as to make the most stable carbocation Halogen anion captures the carbocation Step 1 Step 2 + + 6 +
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Addition of HX to alkene 7 Predict the product of the following reaction. +
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Mechanism of adding HX to alkene 8
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Insight into regioselectivity of HX addition 9 Carbocation (Less stable) 2 o Carbocation (more stable)
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8.5 Carbocation intermediate can rearrange 10 Hydride shif
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11 Hydride shif If carbocation formed by protonation of alkene can be stabilized by rearrangement- it will 8.5 Carbocation rearrangements
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8.6 Acid catalyzed hydration of alkenes ** Acid is the catalyst. Sulfuric acid is used instead of HX to avoid nucleophile competition. 12 Alkene Water Alcohol (cat.)
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8.6 Acid catalyzed hydration of alkenes 13
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8.6 Mechanism of Acid catalyzed hydration of alkenes Step 1
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