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    Organic Chemistry 2 Homework 2: Vo Lam Hoai Trung BTCEIU19009

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    Trung Võ
    This document contains homework problems from an organic chemistry class. It includes reaction mechanisms and identifying structures of compounds. The key information provided includes: 1) Reaction mechanisms involving NaNH2, CH3Br, methylmagnesium bromide, mercury acetate, sodium borohydride, sodium sulfide, sodium, ethyl chloride, and hydrobromic acid. 2) Structures identified for compounds including esters, alcohols, ethers, halides, and a 1,4-disubstituted cyclohexane. 3) An alkoxymercuration-demercuration reaction is described for nucleophilic attack at the most substituted position of an alkene.

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    Organic Chemistry 2 Homework 2: Vo Lam Hoai Trung BTCEIU19009

    Uploaded by

    Trung Võ
    61 views4 pages
    This document contains homework problems from an organic chemistry class. It includes reaction mechanisms and identifying structures of compounds. The key information provided includes: 1) Reaction mechanisms involving NaNH2, CH3Br, methylmagnesium bromide, mercury acetate, sodium borohydride, sodium sulfide, sodium, ethyl chloride, and hydrobromic acid. 2) Structures identified for compounds including esters, alcohols, ethers, halides, and a 1,4-disubstituted cyclohexane. 3) An alkoxymercuration-demercuration reaction is described for nucleophilic attack at the most substituted position of an alkene.

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    HW2

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    This document contains homework problems from an organic chemistry class. It includes reaction mechanisms and identifying structures of compounds. The key information provided includes: 1) Reaction mechanisms involving NaNH2, CH3Br, methylmagnesium bromide, mercury acetate, sodium borohydride, sodium sulfide, sodium, ethyl chloride, and hydrobromic acid. 2) Structures identified for compounds including esters, alcohols, ethers, halides, and a 1,4-disubstituted cyclohexane. 3) An alkoxymercuration-demercuration reaction is described for nucleophilic attack at the most substituted position of an alkene.

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    61 views4 pages

    Organic Chemistry 2 Homework 2: Vo Lam Hoai Trung BTCEIU19009

    Uploaded by

    Trung Võ
    This document contains homework problems from an organic chemistry class. It includes reaction mechanisms and identifying structures of compounds. The key information provided includes: 1) Reaction mechanisms involving NaNH2, CH3Br, methylmagnesium bromide, mercury acetate, sodium borohydride, sodium sulfide, sodium, ethyl chloride, and hydrobromic acid. 2) Structures identified for compounds including esters, alcohols, ethers, halides, and a 1,4-disubstituted cyclohexane. 3) An alkoxymercuration-demercuration reaction is described for nucleophilic attack at the most substituted position of an alkene.

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    of 4

    Vo Lam Hoai Trung

    BTCEIU19009

    ORGANIC CHEMISTRY 2
    Homework 2
    13.34
    1) NaNH2 1) NaNH2 Na, NH3(l) CH3CO3H O

    2) CH3Br 2) CH3Br
    Lin
    dla H2 ,
    r' s
    ca
    tal
    ys O
    t CH3CO3H

    13.37
    a.

    1) CH3CO3H
    2)MeMgBr OH
    3)H2O
    C
    H3

    r
    C

    gB
    O3

    H M
    H

    2) Me
    2O
    1)

    O
    (Racemic)

    b.
    1) Hg(OAc)2, MeOH

    2) NaBH4 OMe

    (Racemic)
    c.
    MeS
    1) CH3CO3H
    2)NaSMe OH
    3)H2O
    (Racemic)
    3
    3

    2
    O
    (Racemic)

    d.
    OH 1) Na OEt

    2) EtCl

    e.
    OH 1) Na O

    2) O OH

    3) H2O

    O
    Na

    2O
    1)

    2) H

    ONa

    f.
    OH
    Cl 1) Mg, diethyl ether

    2) O

    3) H2O
    13.38
    a.

    O HO
    O H H
    O

    CH2CH3

    b.

    H Et I
    O H O O Et

    c.

    O
    O H H HO
    O

    C C H

    d.
    H H
    H O OH
    O H O

    SMe MeS

    13.40
    We have the structure of cis-1,4-dibromocyclohexane: (C6H10Br2)

    Br Br

    Since the structure of the compound B and product have the same number of C and H, we can
    expect that the bond that are cleavage through the reaction is 2 C-O bonds to replace by 2C-Br
    bonds in products and retain the cyclohexane ring. And with the treating reagent is HBr, we can
    expect the compound B have structure of ether (which have no π bonds presents) with the C -O –
    C bonds at 1,4 location in the cyclohexane ring. So the structure of compound B is:
    O Con.c HBr
    O Br Br
    13.42
    In both case a) and b) we will have the Alkoxymercuration – Demercuration reaction in which
    the nucleophile (MeO- and PhO-) will attack in the more substituted position in πbond.
    a.
    1) Hg(OAc)2, MeOH
    OMe
    2) NaBH4

    b.
    OH

    1) Hg(OAc)2 O

    2) NaBH4

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