lecture 24 - Carbon-Carbon Bond Formation and Synthesis...

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1 24 -1 Carbon Carbon -Carbon Bond Carbon Bond Formation and Formation and Synthesis Synthesis Chapter 24 24 -2 Sections 24.6 and 24.7 Sections 24.6 and 24.7 24 -3 Diels -Alder Reaction Alder Reaction ± Diels Diels -Alder reaction: Alder reaction: a cycloaddition reaction of a conjugated diene and certain types of double and triple bonds dienophile dienophile : diene-loving Diels Diels -Alder adduct: Alder adduct: the product of a Diels-Alder reaction 24 -4 Diels Diels -Alder Reaction Alder Reaction Diels-Alder adduct O 3-Buten-2-one (a dienophile) 1,3-Butadiene (a diene) + O 24 -5 Diels -Alder Reaction Alder Reaction alkynes also function as dienophiles cycloaddition reaction: a reaction in which two reactants add together in a single step to form a cyclic product 24 -6 p.967 Diels Diels -Alder Reaction Alder Reaction we write a Diels-Alder reaction in the following way The arrows are used to show which bonds are broken, which new bonds are formed, and how many electrons are involved
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2 24 -7 Diels Diels -Alder Reaction Alder Reaction The special value of D-A reactions are that they (1) form six-membered rings (2) form two new C-C bonds at the same time (3) are stereospecific and regioselective Adduct 24 -8 Example Example Draw a structural formula for the Diels-Alder adduct formed by reaction of each diene and dienophile pair a) 1,3-Butadiene and propanal b)
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lecture 24 - Carbon-Carbon Bond Formation and Synthesis...

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