Chem210-1 F07 Ex1 p02a

Chem210-1 F07 Ex1 p02a - best resonance form you can for...

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3. Consider compound 'A' on the right: H C C C H H H = "A" a) what functional group is present in "A"? (2 pts) _______________________________ b) how many sp 3 C's are present in "A"? ___ 1 _____ how many sp 2 ? ___ 0 ____ sp? ___ 2 ____(2 pts) c) what is the geometry at the carbon atom that has no H's attached? _____ l i n e a r ____ (2 pts) d) Compound "A" might not ordinarily be considered a proton donor, but in the presence of an excess of very powerful bases, two protons can be removed, sequentially, from that structure - each of those two protons is removed from a different carbon atom of the molecule. Give the full Lewis structure (all atoms, bonds (as sticks), lone pairs and formal charges) for the conjugate base form of "A" after it has undergone the removal of two protons as described above (4 points) e) One can draw a resonance form for the conjugate base species in question (d). Provide the
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Unformatted text preview: best resonance form you can for your answer in (d) - be sure your new resonance form has full octets around each carbon (4 points) f) Even using the extremely powerful bases required to carry out the deprotonations described above, an a l k a n e like propane can NOT be deprotonated in the manner that "A" can. Pick either of the two sites undergoing deprotonation in "A"; specify it (you can use the structure at the top); and explain BRIEFLY what makes that site acidic enough to allow deprotonation. (4 points) alkyne C C C H H C C C H H (2-) H C C C H H H C A C B at C A : carbon is sp-hybridized; greater degree of s-character helps stabilize conjugate base at C B : removal of proton leaves a carbanion which can be stabilized by delocalization with one of the π-βονδσοφτηε αδϕαχενττριπλε βονδ...
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