Reaction of R-3-bromo-1-pentene with a) NBS in CCl4 b) Tertiary Butoxide State the products and their R/S configuration:

asked by @evanz3 • over 1 year ago • Organic ChemistryAddition Reagent Facts • 5 pts

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3 answers

Hey Evan! For this question I'll recommend you to watch the following videos:

Link 1 [Allylic Halogenation] : https://www.clutchprep.com/organic-chemistry/allylic-halogenation-2/?c_id=12928#content-item-5083

Link 2 [E2 Elimination reaction]: https://www.clutchprep.com/organic-chemistry/e2-mechanism-introduction/?c_id=7681#content-item-2295

Link 3 [Big Daddy Flowchart]: https://www.clutchprep.com/organic-chemistry/big-daddy-mechanism-flowchart/?c_id=7681#content-item-2495

I've attched the answer below. Let us know if you need any other help. enter image description here

answered by @abdullah • over 1 year ago

Question - Is it not acceptable to make my answers in cyclo-form? I've looked over my answers and they look identical to the line structure but just in cyclic form. Should I touch base with my professor to see about partial credit or would this be a waste of time?

Thanks for your input!

answered by @evanz3 • over 1 year ago

Hey Evan! There is no way we can get cyclic structure in this reaction. Further, cyclic structures and line structures cannot be identical to each other. Cyclic structure is only possible when there exists a nucleophile/base and a leaving group within a same molecule. Also, the cyclisation must form 5 or six member ring. In this question, if you observe we cannot get a five membered ring (even if you are thinking double bond as a nucleophile and bromine as leaving group in the same molecule). I would not suggest to ask for any partial credit from your professor rather it would be more helpful to review the videos I attached for review in the previous comment.

I hope this helped. Let us know if you have any other question :-)

answered by @abdullah • over 1 year ago