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    This document describes a three step synthesis of an alkene. In the first step, an E2 elimination reaction uses a bulky base to remove bromine and form a double bond. The second step adds chlorine across this double bond through halogenation to form a vicinal dihalide. The final step uses a strong base to deprotonate the vicinal dihalide, eliminating hydrochloride to yield the final alkene product.

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    Multi step synthesis

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    This document describes a three step synthesis of an alkene. In the first step, an E2 elimination reaction uses a bulky base to remove bromine and form a double bond. The second step adds chlorine across this double bond through halogenation to form a vicinal dihalide. The final step uses a strong base to deprotonate the vicinal dihalide, eliminating hydrochloride to yield the final alkene product.

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    © All Rights Reserved
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    25 views1 page

    Multi Step Synthesis

    Uploaded by

    gs7514424
    This document describes a three step synthesis of an alkene. In the first step, an E2 elimination reaction uses a bulky base to remove bromine and form a double bond. The second step adds chlorine across this double bond through halogenation to form a vicinal dihalide. The final step uses a strong base to deprotonate the vicinal dihalide, eliminating hydrochloride to yield the final alkene product.

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    © All Rights Reserved
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    of 1

    Mutistepsynthesis problem

    Br

    Br
    t bulk

    In the rst step, an E2 elimination reaction occurs. Potassium tert-butoxide is a


    strong, bulky base that can eliminate Br and form the double bond. This favors the
    the formation of the less substituted alkene (Hofmann product).
    11

    02 01

    In the second step, a vicinal dihalide is formed from an alkene using halogenation, speci cally
    halogen addition reaction. This involves the addition of chlorine (2 halogen atoms) across the
    carbon carbon double bond to result in a vicinal dihalide.

    Il

    II Xs Na Nitz
    2 H2O
    Finally, the vicinal dihalide reacts with excess sodium amide in the presence of water to undergo
    an elimination reaction. The strong base, NaNH abstracts a proton from one of the carbon atoms
    adjacent to the chlorine atom. The phenylacetylene is neutralized by H2O. The removal of
    hydrogen and chloride ion leads to the formation of the alkene.

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