Write the structure of the major organic product of the reaction of 1-bromopropane with (a) NaCN in acetone (b) NaOCH3 in CH3OH (c) (CH3)3COK in (CH3)3COH

asked by @student25478 • about 1 year ago • Organic Chemistry • 5 pts

The answer key shows a and b as SN2 reactions and the third as an E2 reaction. How can a primary leaving group go through elimination?

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1 answer

Hey there! I've posted how the structures would look like after each reaction. For C, it would go through E2 since (CH3)3COK is a bulky base and would be sterically hindered to do SN2. This flowchart can really help you with identifying reactions: https://www.clutchprep.com/organic-chemistry/big-daddy-mechanism-flowchart/?c_id=491

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I hope this helps!

answered by @leot1 • about 1 year ago