Problem: In each reaction box, place the best reagent and conditions from the list below

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We're being asked to determine the best reagents and condition for the given reaction.



Notice that we went from a 2-carbon alkyne to a 5-carbon carboxylic acid.


Step 1: Recall that alkynides can be formed via deprotonation of terminal alkynes. Alkynides react with 0˚ and 1˚ halides via an SN2 reaction to elongate a carbon chain.



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In each reaction box, place the best reagent and conditions from the list below

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What scientific concept do you need to know in order to solve this problem?

Our tutors have indicated that to solve this problem you will need to apply the Redox Retrosynthesis concept. If you need more Redox Retrosynthesis practice, you can also practice Redox Retrosynthesis practice problems.

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Based on our data, we think this problem is relevant for Professor Clizbe's class at UB.