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  • Synproblems An

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    Esther Cruz
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    1. Synthesize 1-chloro-2-butyne from 1-hexene using chloroform, lithium, and ammonia, followed by potassium hydroxide, sodium amide, and iodomethane. 2. Synthesize 3-bromo-1-butyne from 1-butyne using borane, sodium hydroxide and hydrogen peroxide, followed by sodium amide and bromine. 3. Synthesize 1-octyne from octane using hydrogenation with palladium, followed by sodium amide, ammonia, and bromoethane.

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    1. Synthesize 1-chloro-2-butyne from 1-hexene using chloroform, lithium, and ammonia, followed by potassium hydroxide, sodium amide, and iodomethane. 2. Synthesize 3-bromo-1-butyne from 1-butyne using borane, sodium hydroxide and hydrogen peroxide, followed by sodium amide and bromine. 3. Synthesize 1-octyne from octane using hydrogenation with palladium, followed by sodium amide, ammonia, and bromoethane.

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    9 views1 page

    Synproblems An

    Uploaded by

    Esther Cruz
    1. Synthesize 1-chloro-2-butyne from 1-hexene using chloroform, lithium, and ammonia, followed by potassium hydroxide, sodium amide, and iodomethane. 2. Synthesize 3-bromo-1-butyne from 1-butyne using borane, sodium hydroxide and hydrogen peroxide, followed by sodium amide and bromine. 3. Synthesize 1-octyne from octane using hydrogenation with palladium, followed by sodium amide, ammonia, and bromoethane.

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    of 1

    Some Organic Synthesis Practice Problems:

    Starting from 1-hexene, 1-butyne, bromoethane, iodomethane and any reagent needed
    (you do not need to use all of these compounds), synthesize:

    1.
    Cl Cl CHCl3,
    Li, NH3
    KOH
    H3C C C CH2CH3

    NaNH2,
    NH3, CH3I

    H C C CH2CH3

    2.
    1) BH3
    O 2) NaOH, H2O2
    H2O
    H3CH2CH2CH2C C CH
    H

    NaNH2

    Br2
    Br
    Br

    3.
    H2, Pd
    octane H3CH2CH2CH2C C C CH2CH3

    NaNH2, NH3
    CH3CH2Br
    H3CH2CH2CH2C C CH
    see above

    4.
    OH 1) OsO4
    2) NaHSO3 Li, NH3
    H3CH2C C C CH2CH3
    OH
    (racemic) NaNH2, NH3
    CH3CH2Br

    HO OH
    H3CH2C C CH
    H
    H 1-butyne

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