11-04 - Alkene Addition Reactions Nucleophile reacts at carbon that forms most stable carbocation H H CH3 H OH H2SO4 H2O No rearrangement H Give a

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
11/4/2009 1 Alkene Addition Reactions CH 3 H H H OH H 2SO4 H 2O Nucleophile reacts at carbon that forms most stable carbocation No rearrangement! 34 Give a synthesis of the following alcohol: Use electrophilic addition to an alkene as the last step. Start with any compound with four carbons or less. Use any inorganic reagents you need. You will need more than one reaction. Which of these routes is best? A H H NaNH 2 Br H 2 Pd 1. Hg(OAc) 2 2. BH 4 - 35 B C D CH 3 H NaNH 2 Br Na NH 3 H H NaNH 2 H 2 Lindlar CH 3 H NaNH 2 1. Hg(OAc) 2 2. BH 4 - H 2 O H 2 SO 4 H 2 O H 2 SO 4 H 2 Lindlar Regiochemistry? Alkene Addition Reactions CH 3 H H H OH H 2SO4 H 2O 36 Oxymercuration and acid-catalyzed hydration have the same regiochemistry . Synthesis of Alcohols from Alkenes 37 But what if you want the primary alcohol? How do you switch the regioselectivity? An acid will add to the less-substituted carbon± ±to make the more stable 2° carbocation 38 Boron can form stable bonds with carbon Tricoordinate Boron compounds are Lewis Acids.
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Image of page 2
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 12/25/2009 for the course CHE 320 taught by Professor Ff during the Spring '09 term at SUNY Stony Brook.

Page1 / 5

11-04 - Alkene Addition Reactions Nucleophile reacts at carbon that forms most stable carbocation H H CH3 H OH H2SO4 H2O No rearrangement H Give a

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online