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Carbonyl Group

Carbonyl Group. Can the carbonyl act as a Lewis (or Bronsted ) base? a. yes b. no. Carbonyl Group. Can the carbonyl act as a Lewis acid? a. yes b. no. Acidic Conditions Mehcanism (Acid Catalyzed). Stability Given that What is the order of stability?

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Carbonyl Group

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

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

  3. Acidic Conditions Mehcanism(Acid Catalyzed) Stability Given that What is the order of stability? a. A>B>C b. C>B>A c. B>C>A d. 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. Acetal Formation Mechanism Under Acidic Conditions

  8. 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.

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

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

  11. Cyanohydrin Reaction • How would NH3 normally react with an aldehyde? • Form an amine b. Form an alcohol • Form an acetal d. Form an imine e. Form a hemiacetal

  12. Cyanohydrin Reaction • To what class does this compound belong? a. carbohydrate b. steroid c. alkaloid d. amino acid e. fatty acid • Strecker synthesis

  13. Cyanohydrin Reaction • NH4Cl releases NH3. 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. SN1 b. SN2 c. E1 d. E2 e. Electrophilc Addition

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