272_quiz1_solutions - A B C D D> A> C> B This...

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Chain Chem 272 Quiz 1 1. Answer the following questions about the hydrocarbon shown below. H 3 C H a. Label the shortest carbon–carbon single bond A b. Label the longest carbon–carbon single bond B c. Label the shortest carbon–carbon bond C d. Label the strongest carbon–hydrogen bond D e. Put a circle around an sp-hybridized carbon f. Put a box around an sp 3 -hybridized carbon 2. Label and rank the four most acidic protons in the molecule shown below. H 2 N O NH 2 OH OH O most acidic least acidic 3. The molecule shown below is ascorbic acid (vitamin C). Circle the most acidic proton in vitamin C. O O OH OH HO HO BONUS: A picture is worth a thousand words. Why did you pick the proton you did in question 3? Show me one picture to justify your answer. Name: A B C D This question is all about recognizing hybridization states. Shorter and stronger bonds are made using orbitals of higher 's-character'.
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Unformatted text preview: A B C D D > A > C > B This question is all about recognizing the stability of conjugate bases. The most important factors when considering conjugate base stability are the electronegativity of the atom(s) bearing the charge, and resonance delocalization. Deprotonating any of the oxygens in this molecule results in an oxyanion. Two are localized onto a single atom (the two oxygens on the lower left), and two have the benefit of resonance delocalization (the two oxygens on the right). The circled OH group, when deprotonated can has more resonance structures, and enjoys delocalization onto the carbonyl oxygen. The other oxygen does not (you can only push those electrons onto a carbon atom). O O OH O HO HO O O OH O HO HO Answer Key...
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