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    Quiz Chapter 12 - Alcohols From Carbonyls

    Uploaded by

    Karan Randhawa
    Here are the predicted products from the reactions: (a) 3-pentanol (b) 1-phenyl-1-propanol (c) 2-methyl-2-butanol (d) deuteroethane (e) ethane (f) ethane (g) ethane (h) extensive elimination to ethylene The organometallic reagent ethylmagnesium bromide will undergo alkylation with the carbonyl compounds (a-c), resulting in secondary alcohols after acidic workup. Compound (d) will undergo isotopic exchange. The carboxylic acid and alcohol (f-g) will not undergo reaction and will

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    Quiz Chapter 12 - Alcohols From Carbonyls

    Uploaded by

    Karan Randhawa
    101 views16 pages
    Here are the predicted products from the reactions: (a) 3-pentanol (b) 1-phenyl-1-propanol (c) 2-methyl-2-butanol (d) deuteroethane (e) ethane (f) ethane (g) ethane (h) extensive elimination to ethylene The organometallic reagent ethylmagnesium bromide will undergo alkylation with the carbonyl compounds (a-c), resulting in secondary alcohols after acidic workup. Compound (d) will undergo isotopic exchange. The carboxylic acid and alcohol (f-g) will not undergo reaction and will

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    Here are the predicted products from the reactions: (a) 3-pentanol (b) 1-phenyl-1-propanol (c) 2-methyl-2-butanol (d) deuteroethane (e) ethane (f) ethane (g) ethane (h) extensive elimination to ethylene The organometallic reagent ethylmagnesium bromide will undergo alkylation with the carbonyl compounds (a-c), resulting in secondary alcohols after acidic workup. Compound (d) will undergo isotopic exchange. The carboxylic acid and alcohol (f-g) will not undergo reaction and will

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    101 views16 pages

    Quiz Chapter 12 - Alcohols From Carbonyls

    Uploaded by

    Karan Randhawa
    Here are the predicted products from the reactions: (a) 3-pentanol (b) 1-phenyl-1-propanol (c) 2-methyl-2-butanol (d) deuteroethane (e) ethane (f) ethane (g) ethane (h) extensive elimination to ethylene The organometallic reagent ethylmagnesium bromide will undergo alkylation with the carbonyl compounds (a-c), resulting in secondary alcohols after acidic workup. Compound (d) will undergo isotopic exchange. The carboxylic acid and alcohol (f-g) will not undergo reaction and will

    Copyright:

    © All Rights Reserved
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 16

    Predict the IR absorption bands

    that would allow you to ID each


    compound in pairs
    O

    H3C CH3 H3C OH

    1722 cm-1 3320 cm-1

    O O
    CH3
    H3C OH H3C O

    C=O 1712 cm-1 C=O 1742 cm-1


    O-H 3000 cm-1 (broad) no OH absorption present
    What products would you expect from the reaction
    of CH3CH2MgBr followed by 2. H3O+

    1. MgBr
    O
    H2N ether

    +
    2. H 3O

    HO HO O
    H2N H2N H2N

    1 2 3
    What products would you expect from the reaction
    of CH3CH2MgBr followed by 2. H3O+
    1. MgBr
    O
    HO ether

    +
    2. H 3O

    HO HO O

    HO HO HO

    2 3
    1
    How would you prepare compound 1?

    O HO
    HO HO

    Protect phenolic OH group 1


    (CH3) 3SiCl / NEt 3

    1. MgBr
    O OH
    (CH 3) 3SiO ether HO
    +
    2. H 3O
    + -
    3. (Bu) 4N F
    What products would you expect from the
    reaction of 1. ethylmagnesium bromide (CH3CH2MgBr)
    followed by 2. H3O+ with each of the following reagents?

    O 1. MgBr
    H
    ether

    +
    2. H 3O

    OH OH
    H OH H H

    1 2 3
    How would you prepare molecule 2 from
    2-phenylethanol

    OH OH

    1 2

    1. PCC 2. CH3MgBr
    PCC or swern
    oxidation or swern 3. H 3O
    +
    oxidation
    1. MgBr
    O OH
    ether

    +
    2. H 3O
    How would you prepare methylcyclohexane
    from cyclohexanone in 3 steps?
    O CH3

    1. CH 3MgBr H2
    +
    2. H 3O Pd

    HO CH3 CH3
    H2SO4

    heat
    Chiral ?? Achiral
    --------------
    C≡
    C
    C≡C-
    H

    CH3CH2CH2CH2-C≡C-H

    1-HEXYNE
    Match the following IR spectra to one of
    the given chemical structures

    O-H C=O
    1720 cm-1
    3500 3000 2000 1500 1000 cm-1
    O O
    H3C CH3 O CH3
    H3C NH2
    O
    CH3 H3C
    CH3 O
    HO CH3
    CH3

    I II III IV
    OXIDATIONS

    OH PCC in CH2Cl2 O

    Or Swern oxidation
    1. DMSO (COCl)2
    2. NEt3

    OH Jones reagent O

    H2CrO4 in H2SO4 OH

    Or KMnO4 / H2O /-OH


    Which of the following are
    organometallic reagents ?
    No, sodium attached to
    oxygen not carbon
    (a) CH3CH2ONa (b) CH3CH2Li
    No, boron is not a metal
    (c) CH3CH2BH2 (d) (CH3CH2)2Zn

    (e) CH3CH2MgBr (f) CH3C≡CNa


    11
    O O OH O

    * O CH3
    O CH3

    NaBH4
    1 equiv. H2 CH3OH
    Pd, CH3CH2OH O O

    O CH3

    1. LiAlH4, THF
    2. H2O
    OH
    *
    OH

    12
    What is the major organic product
    obtained from the following reaction?

    O
    OH OH

    PCC 1 2
    OH O
    CH2Cl2

    HO
    H OH
    3 4

    13
    What are the main products of the
    reaction of each of the following with
    ethyl magnesium bromide followed by
    a regular acidic work-up ?
    (a)CH3CH2CHO 3-pentanol - CH CH CHOHCH CH
    3 2 2 3

    (b) C6H5CHO 1-phenyl-1-propanol - C H CHOHCH CH


    6 5 2 3

    (c)CH3COCH3 2-methyl-2-butanol, (CH ) COHCH CH


    3 2 2 3

    (d) D2O deuteroethane, CH3CH2D


    14
    (f) C6H5CO2H ethane, CH3CH3(due to acidic H)

    (g) CH3CH2OH ethane, CH3CH3(due to acidic H)

    (h) CH3CH2Br no useful Extensive elimination


    reaction CH2=CH2

    15
    O OH
    CH3
    CH3
    CH3
    H3C CH3

    H3O+
    +
    O MgBr
    δ- δ+ CH3
    CH3MgBr
    H3C CH3

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