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OSU / Chemistry / CHEM 2510 / What are examples of diel alder's reactions?

What are examples of diel alder's reactions?

What are examples of diel alder's reactions?

Description

School: Ohio State University
Department: Chemistry
Course: Organic Chemistry I
Professor: Christopher callam
Term: Summer 2016
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Cost: 50
Name: OCHEM Study Guide
Description: This are concepts on the final
Uploaded: 12/11/2016
11 Pages 138 Views 2 Unlocks
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  • Examples of Diene Stereochemistry
  • If both groups have the same descriptor (both point out or in), they both must end up on the same side.
  • s-cis confirmation
  • 1%
  • Except...this reaction would not work

  • This would not work because this confirmation is very high energy and would only appear 1% of the time compared to its s-cis counterpart.
  • If groups point in different directions → trans
  • Ranged DIenes
  • Group 1s pointing in so carbon must be connected to both 3 and C
  • Other examples: putting it all together

  • Diene, alkene → major → groups under
  • Callam’s simpler way
  • In ends up wedged
  • Out ends end up dashed
  • Endo- carbonyl under the main ring. Usually, the main product because nonbound orbitals stabilizes it,
  • Exo- pointed away from the ring.

  • Diels Alder with Alkyne
  • No stereochemistry because flat sp 2
  • 2 possible combinations
  • But which one is the right orientation of ?
  • Draw out the resonance structure to show partial charges
  • You want to look at the carbons because we are making C - C bonds.
  • Right regio stereochemistry vs wrong regio stereochemistry

  • HOMO and LUMO must interact
  • 2 HOMO cannot work because too many electrons
  • 2 LUMO = no because no electrons
  • Diels Alder Reactions Examples

Example:

  •  →
  • diene s-cis conformation and alkene-(Z) geometry (along for the ride)
  •  Need a conjugated diene.
  • Diels alder requires s-cis geometry diene
  • (Z) geometry creates functional groups that are on the same side
  • (1) → (2) (E) geometry → (3) (E) geometry= functional groups on opposite sides of || bond.                                         H- X addition
  • Geometry of Dienes in Diels Alder
  • (1) s-trans [usually lowest energy conformation] → (2) → (3) s-trans, can’t be rotated so no diels alder → (4) s-cis only so very fast diels alder reaction → (5)
  • Kinetic product- favored at lower reaction temperatures short reaction time.
  •  Thermodynamic product- favored at high temperatures, long reaction time.
  • Doesn’t matter what forms first, what matters is the more stable product forms.

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  • Examples of H- Br Addition to Dienes
  • |r| substituted
  • --(H- Br)--(0 o. C) → low reaction temperature, kinetic product forms
  • More stable = thermodynamic product
  • --(H- Br)--(50 o. C) → thermodynamic product forms
  • Example %2: H- Br Addition to Dienes
  • --(H- Br)--(0 o. C) →
  • No difference, equal products
  • 1,2 addition does not always give you less stable products
  • Diels Alder Reactions
  • 2 𝝅 electrons, 4 𝝅 electrons → cyclohexene
  • 1. Number of bonds
  • 2. Draw cyclohexene frame
  • 3. Draw other groups
  • [4+2] cycloaddition reaction
  • Requires heat and pressure
  • Always creates cyclohexene
  • Concerted, exothermic reaction
  • Molecular Orbital Theory
  • Alkene
  • 1 𝝅 bond
  • 2 𝝅 electrons
  • 2 p orbitals ← for every pi bond there are 2 p orbital overlaps
  •  Diene
  • 2 pi bonds
  • 4 pi bonds
  • 4 p orbitals
  • You should have the same number of antibonding orbitals as bonding orbitals
  • Can’t have electrons there, because too high of energy requirement

  •  node= where electrons are not communicating with each other.
  • Antibonding LUMO (lowest unoccupied molecular orbital)
  • idea= separation, not together,
  • HOMO (highest occupied molecular orbital)
  • Lowest energy state, we have lowest p 1 bond overlap.
  • Bonding molecular object

  • 𝝅 4 → 3 nodes → antibonding orbitals
  • 𝝅 3 → 2 nodes → antibonding orbitals, LUMO
  • 𝝅 2 → 1 node → bonding orbitals, HOMO
  • 𝝅 1 → 0 nodes → (resonance hybrid) bonding orbitals, HOMO
  • Nodes: electron density equal across all planes

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