Summary: Organic Chemistry 2

Read the summary and the most important questions on Organic Chemistry 2

• 1 lecture 1

• 1.2 stability

• What are resonance contributors?

  Mesomeric/resonance structures, sigma bonds remain intact, p-electrons and lone pairs move

• Is a molecule with localized charge more or less stable than one with delocalized charge, and is it more or less acidic?

  Less stable and thus less acidic

• 1.5 Sn2

• what are 4 characteristics of a Sn2 reaction?

  1. Concerted (one step) mechanism
  2. Backside attack
  3. Inversion of configuration
  4. Sp2 hybridized transition state

• 1.6 Sn1

• What are 4 characterisitcs of a Sn1 reaction?

  1. Two step mechanism
  2. Racemisation in case of substitution at stereocenter
  3. Depends only on concentration of starting material
  4. (possible) rearrangement of carboskeleton

• What is the order of stability of carbocations?

  Tertiary>secondary>primary

• 1.7 E2

• What are 2 characteristics of E2?

  1. Concerted (one step) mechanism
  2. Most substituted alkene is formed

• When is elimination favored?

  With a strong base

• What is Hofmann elimination and when does it occur?

  Less substituted alkene is formed, occurs with strongly electronegative and relatively poor leaving groups (F, N+, S+)

• 1.8 E1

• What are 2 characteristics of E1?

  1. Rate is dependent only on the concentration of the halide
  2. Two step mechanism, intermediate is formed

• 1.9.1 converting alcohols into alkyl halides

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• For which alcohols is heat needed to convert it into an alkyl halide, primary, secondary or tertiary?

  Primary and secondary need heat