Chemistry 2213A/B Study Guide - Final Guide: Tautomer, Fischer Projection, Cyclopentane

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Carbonyl group is present in both aldehydes and ketones. In aldehydes, bonded to at least one hydrogen. Both the c and o are sp2 hybridized (p orbitals overlap to form pi bonds: angles are 120o. Carbonyl reactivity: higher b. p. than ethers, but lower than alcohols. If we draw the resonance structure of the carbonyl group, we can see that: electrophiles add to oxygen, nucleophiles add to carbon. This resonance contributes to the bond polarity. This is the most common reaction of aldehydes and ketones. Since nucleophiles and electrophiles always add to the same position, only one regioisomer is possible for these reactions. The mechanism depends on whether the reaction occurs in acidic or basic conditions. Nucleophilic additions because the rds is the breaking of the pi bond by the nucleophile. Anions are present in basic solution nucleophilic attack occurs first.

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