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  • 8/14/2019 Perception test 4 organic chem sem 2.docx

    1/5

    Perception test 4 organic chem sem 2

    1)1 of 20

    Malonate chemistry is used since the protons are____more__ acidic than inketones.

    The acidity of malonate protons is about __13___on the pKa scale

    2)2 of 20

    Identify the product of the reaction between PhMgBr and acetaldehyde (CH3CHO):

    Phenol -1benzyl-ethan-1-ol

    Diphenylmethane 2-mgbr phenol

    3)3 of 20Identify the product of the reaction between PhMgBr and acetone (CH3COCH3):-2-benzylpropan-2-ol

    1-benzylmethanol

    diphenylmethanol

    mgbr isobutanol benzene

    4)4 of 20

    Identify the product of the reaction of PhMgBr with carbon dioxide

    PhCH2OH

    Benzene

    Ph-Ph

    -PhCO2H

    5)5 of 20

    Identify the product of the reaction with C2H5CO2C2H5with MeMgBr

    C2H5COC2H5

    (C2H5)2C(OH)CH3

    C2H5C(OH)(CH3)2

    CH3COC2H5

    6 of 20

    Rank the following compounds in terms of acidity (most acidic first):

    EtOH most acidic acidic less acidic xleast acidicPhOH most acidic acidic xless acidic least acidic

    ClCH2CO2H xmost acidic acidic less acidic least acidicCH3CO2H most acidic x acidic less acidic least acidic

    7

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    7 of 20

    Use the arrow to indicate the most acidic protons in the following compound:

    Aldehyde alpha protons

    8)8 of 20

    Use the arrow to indicate the bond polaiziation in a carbonyl compound:

    Carbonyl bond9)9 of 20

    Rank the following carbonyl compounds in order of reactivity with nucleophiles:

    aldehyde mostreactive Reactive

    x lessreactive

    leastreactive

    Ketone mostreactive reactive

    lessreactive

    X leastreactive

    anhydride mostreactive

    x

    reactiveless

    reactiveleast

    reactive

    acid chloride mostxreactive reactive

    lessreactive

    leastreactive

    10)

    10 of 20Identify the product of thefollowing reaction of C2H5COClwith MeCuLi

    C2H5COC2H5

    C2H5C(OH)(CH3)2

    (C2H5)2C(OH)CH3

    -->CH3COC2H5

    ketone

    11)

    11 of 20

    Place the arrow on the product of the following reaction:

  • 8/14/2019 Perception test 4 organic chem sem 2.docx

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    12 of 20

    Use the arrow to indicate which of the following compounds is not prone to decarboxylationwhen heated:

    Cyclohexane based one

    13 of 20

    Indicate the reagents required to carry out the following transformation:

    pyran in a acidic environment

    14 of 20

    To which side does the following equilibrium lie:

    reaction does not occur

    -to the right

    equally to left and right

    to the left

    15 indicate product of rxn

  • 8/14/2019 Perception test 4 organic chem sem 2.docx

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    Addition and formation of double bond imine not c2h3

    16)

    16 of 20

    Which of the following is the product of the reaction of LiAlH4with C2H5CONHC2H5

    C2H5CH2OH

    C2H5NH2

    C2H5CH2NH2

    -C2H5CH2NHC2H5

    17)

    17 of 20

    Which of the following reagents will produce the desired reaction show below:

    MeMgBr, then EtMgBr

    MeLi, EtI

    -->NaOEt, MeI, then NaOEt, EtI

    NaOEt, MeMgBr, then NaOEt, EtMgBr

    18 of 20

    Use the arrow to indicate the reagents required in the following reaction:

    Base cat ethan-1,2-diol-->Acid cat ethan 1,2, diol2Brmg-ethanol

    acid and water

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    19)Which set of reagents are need for the following reaction:(LDA is a strong base)

    -LDA, then PhCH2Br

    CH3MgBr, then PhCH2Br

    PhCH2MgBr, then H3O+

    NaOCH2CH3, CH3I

    20 of 20

    Use the arrow to indicate the product from the follwoing reaction:

    Ketone with 1 carbon additional to alkyl x group.


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