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Nicole_5521
#1 Posted : Friday, July 02, 2021 6:47:30 PM
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Hello,

For Q30 in Altius FL3 Chem section, could you explain how acetylene has an electron deficiency? I thought multiple bonds would make something a lewis base, so having electron density.

Thanks!
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INSTR_Katrina_128
#2 Posted : Monday, July 05, 2021 2:24:18 PM
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This question is very tricky. Boo. 😫

First, the text tells us in paragraph 3 that the amino acid-derived PRO-NUCLEOPHILE was reacted with an acetylene derivative. This implies that the acetylene derivative MUST BE the electrophile.

Note: a pro-nucleophile just means something that can easily BECOME a nucleophile.

So, we have to accept that from the wording of the text, we have an electrophile. Therefore, it's an ACID. Since triple bonds aren't particular acidic, they don't donate H's very well. Therefore, this is not a Brønsted acid. Also, there are no obvious H's to donate. Instead, it's a Lewis acid, which is based on electron transfer.

pKa acetylene = 25 (for example --> indicates that acetylene is a poor H donor)
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