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III. (14 points) Draw the conjugate bases for the deprotonation ofpropanal. Rank

ID: 579561 • Letter: I

Question

III. (14 points) Draw the conjugate bases for the deprotonation ofpropanal. Rank the acidity of the hydrogen atoms, and explain your ranking. most acidic least acidic 13-. Give the correct order A. Ha> Hb>Hc B. Hc> Hb> Ha C. Hb> Hc Ha D. Hb>Ha>Hc Hb H BOXA BOX C BOX B 15-. in BoX B Which structure(s) could go in 14-. BOXA and in 16-. BOX C and be correct? Ha O H Ha Hb Hb Hb 17-. Which concept(s) should be discussed to fully answer this question A) steric hindrance B) hyperconjugationC) resonance D) electronegativity E) oxidation state F) induction G) valence shell_?

Explanation / Answer

The correct order is D

Because proton C is part of aldehyde and it cant be acidic. And then it comes proton B it is most acidic because of resonance with carbonyl group. Proton A which is attatch to sp3 carbom is less acidic, and thus we get the correcr order D

The conjugate acids are,

BOX A = E

BOX B = H ( resonanc )

BOX C = B