SN1 solvolysis: push the electrons yourself
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You just pushed every arrow of the SN1 solvolysis.
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Organic Chemistry 1 · Free interactive demo
tert-Butyl bromide first loses bromide to form a tertiary carbocation, then water attacks to make a protonated alcohol. A second water molecule removes an oxygen proton, giving tert-butanol and hydronium with bromide still present; this exercise follows the substitution branch only.
Draw all four arrows above across three reaction steps. Each arrow is checked as you draw it, and Hint reveals the next move a little at a time.
Turn your own notes into exercises like this one
With the Arrow Lab student plan you can snap a photo of a reaction from your lecture notes or textbook. Arrow Lab reads the starting materials and reagents, you check that reading, and it builds the mechanism as an exercise like the one above: you draw each arrow, get hints when you are stuck, and see right away whether each move is correct.
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The SN1 mechanism, step by step
SN1 substitution separates leaving-group departure from nucleophile attack: the rate-determining ionization depends on the substrate rather than on a collision with the nucleophile. A tertiary carbocation and a polar solvent such as water make this pathway accessible even though water is a weak nucleophile. Water is also the solvent, so the reaction is called solvolysis; elimination can compete but is not drawn in this substitution branch.
The 4 steps of the demo, in the exercise's own words. Try drawing each one above before you read it.
Begin the substitution branch
Ionization occurs before water capture in this specified branch.
Continue from the ion pair
Water capture removes the carbon positive charge and creates oxygen positive charge.
Remove an oxonium proton
Neutral alcohol formation requires loss of one proton; bromide remains present.
Substitution branch products
tert-Butanol is neutral. Hydronium and bromide retain the ion charges; the explicit two-water atom inventory is conserved. This branch does not imply that elimination is absent.
How the mechanism is drawn
Follow only the substitution branch of tert-butyl bromide solvolysis in water; a second explicit water accepts the final proton. Elimination is a competing branch not drawn here.