Question

Exercise 23-1: Aldol Condensation Outcomes: After completing this activity, you should be able to Provide products and mechanisms for aldol and mixed aldol reactions and condensations. Exercise I: Spartan 11.12 Llor) -a 1. Examine atomic charges and display the electrostatic potential map for 2,7-octanedione. Which hydrogens are most likely to be abstracted by a base? Explain your reasoning, 2. Record the energies (Click-Properties-Energy) of the enolates a and b. a: -457.6520 a.u. b: -457.6425 a.u. 3. Which enolate is more stable? 4. Which is kinetically favored enolate? 5. Which is thermodynamically favored enolate? 6. Record the energies of the transition states for the ring closures of a to c and b to d. a toe-457.6242 a.u. b to d -457.6123 a.u. 7. Calculate the activation energy (energy difference between the enolate and the transition state) using the energy values from Q. 2 and 0.6. a toc b to d 8. Which ring closure is expected to occur more readily? 8. Which is expected to be the major product of this reaction?

Answer 1

A Aldol Condensation Hans P-Tron (1.009.) boc, Ismin t hen a P-Tron (1. ep.) 60c, Is ein. Dan b b minor SZI TO Ho Heat en a enolate Thermodynamic endate 1 thì Mey's product -610% N fon Eton b enolate Minoz Product methytene (-ey proton most likely to be bare becaune it is more stable product give membered ring is more stable than abstracted by a will be formed. seven membered - @ The energier a = - 457.6520 anu b = -4576425 aiu ① methylene (-cg) enolate more stable. ② -CH₂ methyl is kinetically favored enolase. 6 (-ch) methylene is the tmodynamically favored onolate. 6 a to c = 457.6242 a.u. (8 C ok, zine membered ring closure is expected to occur - more readily 6 a of five membered is majoz product of the reaction..