Question

please help with organic question 13a, 13b, 13c, 13d and question 14

13. (8 pts) Do the following to fully analyze the proton-transfer reaction shown below a. Annotate the left-hand structures with curved arrows indicating the mechanism of the forward reaction b. Based on the value of the equilibrium constant (Kool, the best description of A runis: 1Gran greater than zero (endergonic) 4Gunless than zero (exergonic) Gran approximately zero fisergonic) c. The transformation can correctly be described as: a Bronsted Acid Base reaction a Lewis Acid Base reaction both of these neither of these d. Which is the stronger acid? both compounds have the same pk, no way to tell 14. (12 pts) in the boxes provided, give a brief explanation for the observed difference in behavion reactivity between each pair of compounds. HC 0:0 is a weaker base than HCCH is a better leaving group than is a more reactive nucleophile than

Answer 1

Q-18 al Base Acid - byty Based on the value of equilibrium constant (tegl, the 44. RTin Kege l ret Ta 298 k • - 8,314 3 2 9 8 x In Joon 11409.6 i molt TaaGo is less than a zero ; ( exergonic). a t the transformation is Bronsted Acid / Base Reaction. I became thicphenotide ion abstracts proton from acetic acid hence this phenoxide acts as Bronsted base f Aretic acid as Bronsted Acid . In Both compounds, (pka = 4,8) becaue baie is stabilised by group. Acetic acid is stronger acid after deprotonation, the conjugate Eri electron withdrawing carbonyl a thiophenol is weak acidic (pka = 10.3).

is weaker bove than than ös uz CH2 In on compound ④ , the ave two electronegative oxygen charge is delocalised atoms hence weak bove. 1 In compound ® the hence stronger bases ove charge is not delocalised, i t A is better leaving group than halda After leaving group departs- In compound oi due to three fluorine atoms, the acetate ion Inductive (-I) effect highly electronegative is stabilized by chlorme is arifluoroacetate less ion electronegative than is better leaving fluorine herre group .

MTWTFS Vate: 1 Page No - is more reactive nucleophile than u - In ove hence case of ④, charge, hence more reactive there is no delocalisation it is readily available nucleophile of for attack An compound there is Resonance Stabilisation etc & ders negative reactive charge is nucleophile, not available for reaction hence