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Carbonyl Group Can the carbonyl act as a Lewis (or Bronsted) base? a. yesb. no.

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Presentation on theme: "Carbonyl Group Can the carbonyl act as a Lewis (or Bronsted) base? a. yesb. no."— Presentation transcript:

1 Carbonyl Group Can the carbonyl act as a Lewis (or Bronsted) base? a. yesb. no

2 Carbonyl Group Can the carbonyl act as a Lewis acid? a. yesb. no

3 Acidic Conditions Mehcanism (Acid Catalyzed) Stability Given that What is the order of stability? a. A>B>Cb. C>B>Ac. B>C>Ad. C>A>B

4 Acetal Formation Mechanism Under Acidic Conditions Cyclic acetals are stable to bases but are unstable in aqueous acids. Why is the cyclic acetal favored? a. Cyclic acetal formation is not entropically unfavorable while the acyclic reaction is. b. A stable 5 membered ring is formed. c. There is more steric hindrance in the acyclic product. d. Methanol is less reactive. e. a. and b.

5 Slide 8 refers to the reactions in Slides 6 and 7

6 Acetal Formation Mechanism Under Acidic Conditions

7

8 Cyclic acetals are stable to bases but are unstable in aqueous acids. Why is the cyclic acetal favored? a. Cyclic acetal formation is not entropically unfavorable while the acyclic reaction is. b. A stable 5 membered ring is formed. c. There is more steric hindrance in the acyclic product. d. Methanol is less reactive. e. a. and b.

9 Addition of Nitrogen Nucleophiles Can we make an imine or imminium ion from 3  amines? a. yesb. no

10 Reactions of Organometallic Compounds Where would the mechanism arrows go in the 1 st step? Where would the mechanism arrows go in the 2 nd step?

11 Cyanohydrin Reaction How would NH 3 normally react with an aldehyde? a.Form an amineb. Form an alcohol c.Form an acetald. Form an imine e. Form a hemiacetal

12 Cyanohydrin Reaction To what class does this compound belong? a. carbohydrateb. steroidc. alkaloid d. amino acide. fatty acid Strecker synthesis

13 Cyanohydrin Reaction NH 4 Cl releases NH 3. This reacts with the aldehyde to make the imine. The cyanide ion then reacts with the imine.

14 Wittig Reaction Initial Reaction What type of reaction is occurring? a. S N 1b. S N 2c. E1d. E2 e. Electrophilc Addition


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