Problem: In each reaction box, place the best reagent and conditions from the list below. (Some reagents may be used more than once.) H2, Pt CH3Br CH3CH2Br NaBH4 NaH H2 Lindlars Catalyst Na, NH3, CH3CH2CH2Br, NaOH, H2O, BH3/THF Br2H2O

🤓 Based on our data, we think this question is relevant for Professor Galarneau's class at Michigan Technological University.

FREE Expert Solution

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


Notice that we went from a 3-carbon alkyne to a 5-carbon epoxide.


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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Problem Details

In each reaction box, place the best reagent and conditions from the list below. (Some reagents may be used more than once.) 

H2, Pt CH3Br CH3CH2Br NaBH4 NaH H2 Lindlars Catalyst 

Na, NH3, CH3CH2CH2Br, NaOH, H2O, BH3/THF Br2H2O


Frequently Asked Questions

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 Addition Retrosynthesis concept. If you need more Addition Retrosynthesis practice, you can also practice Addition Retrosynthesis practice problems.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Galarneau's class at Michigan Technological University.