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Preparation of the Bromohydrin of 3-Sulfolene

A student exoeriment that ~llustrateselectroohilic addition to alkenes is the reaction of N-hromosuccinimide with
3-sulfalene to yield succinimide and ( * ) - t r a n s - 3 - b r o m o - 4 - h y d r o x y - 2 , 5 - d i h y d ~ i d [Becker,
e H. J., Stevens,

d-.. Do2
W., and Dost, N., Ree. Trau. Chim., 67, 451
0 (194811. Thus 1.00-1.50 g of 3-sulfolene, an

+ Q-FI+ equimolar quantity of NBS and 15-20 mL of


water is heated for on a steam bath with oc-
casional swirling for 25-30 min. During the
0 0 Br heating period, students are asked to
1) Verify the presence of the carbon-carbon double bond in 3-sulfolene by the use of aqueous potassium permanga-
nate.

2) Ohserve the action d o ronr~nrratrdaqueous <~rlution o i Nal on 20 mp. s,f NBS, in u hirh iodidp hm rather rhan JIII-

+ .
folene a<Ls as a nucleophile un the d e r r m p h ~ l hnmline
and s h o w the rmrtiuns I- HI-I. [-HI r :I and 1
~r in NHS. l'hs mdme 4 u r that d w e h p s is be-t sern in CCIa
+
I-HI * 1-1 T Br-, where :I is the succinimidr anion.

3) Devise a procedure for isolating the desired product based on its physical properties. This last exercise, approximating
the situation of a practicing chemist who has prepared anew compound, is an effort tocombat "cookhookism"and
allow students to recognize that product isolation is an essential, thought-demanding, and often challenging operation
in synthesis. Students generally seem eager to solve the puzzle and are urged t o consult the instructor before pro-
ceeding. This approach may be adaptable to a numher of preparative experiments.
After emerging from the reaction mixture on chilling in an ice bath, the product is suction-filtered and washed with
cold water. Recrystallization from -10 mL ofwater affords the whlte solid, whose reported mp is 190-191'. Student yields
range fram 40-90%.
The IR spectrum of the hromohydrin compared with that of 3-sulfolene immediately reveals the absorption corresponding
to OH stretching. The trans configuration can be deduced fram the coupling constant of the protons a t carbons 3 and 4 ( J
= 3 Hz) in the decoupled NMR spectrum.
The experiment as given to students is available on request.

Fred H. Greenberg
SUNY College at Buffalo
Buffalo, NY 14222

638 Journal of Chemical Education