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CHEM 350 S’18 Problem Sessions Week 8 Solutions

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1) Making New Carbon Bonds Circle and fill-in the blank: The first step of the reaction involves the protonation / deprotonation of a terminal / internal alkyne. The second step uses the alkyne anion as the nucleophile / electrophile and a R-OH / R-X as the nucleophile / electrophile. Circle all bases below that are sufficiently basic to deprotonate a terminal alkyne and generate Keq >> 1. Remember that the pKa of a terminal alkyne is about 25. Any base that has a conjugate acid with a pKa lower than 25 will NOT deprotonate an alkyne. Circle all of the electrophiles that will react with an alkyne to form a new C-C bond with high yield. ANY methyl or 1o R-X will do! ROH will NOT work.
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