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    Tugas - 6 Senyawa Alkuna

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    Baiq Arin
    This document contains 41 practice questions about organic chemistry reactions involving alkynes. The questions cover drawing Lewis structures of alkynes, naming alkynes using IUPAC nomenclature, describing alkynes' bonding and acidity, drawing reaction mechanisms, and identifying products of addition, substitution, elimination and rearrangement reactions involving alkynes.

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    Tugas - 6 Senyawa Alkuna

    Uploaded by

    Baiq Arin
    65 views3 pages
    This document contains 41 practice questions about organic chemistry reactions involving alkynes. The questions cover drawing Lewis structures of alkynes, naming alkynes using IUPAC nomenclature, describing alkynes' bonding and acidity, drawing reaction mechanisms, and identifying products of addition, substitution, elimination and rearrangement reactions involving alkynes.

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    Tugas_6 Senyawa Alkuna

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    This document contains 41 practice questions about organic chemistry reactions involving alkynes. The questions cover drawing Lewis structures of alkynes, naming alkynes using IUPAC nomenclature, describing alkynes' bonding and acidity, drawing reaction mechanisms, and identifying products of addition, substitution, elimination and rearrangement reactions involving alkynes.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    65 views3 pages

    Tugas - 6 Senyawa Alkuna

    Uploaded by

    Baiq Arin
    This document contains 41 practice questions about organic chemistry reactions involving alkynes. The questions cover drawing Lewis structures of alkynes, naming alkynes using IUPAC nomenclature, describing alkynes' bonding and acidity, drawing reaction mechanisms, and identifying products of addition, substitution, elimination and rearrangement reactions involving alkynes.

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    © All Rights Reserved
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    PRACTICE EXERCISE – ORGANIC CHEMISTRY I

    Alkynes Synthesis and Reactions

    FOR QUESTIONS 1-4, DRAW A LEWIS OR LINE-ANGLE FORMULA AND GIVE THE IUPAC NAME.

    1) (CH3)2C(CH2CH3)CCCH(CH3)2 2) HCCCH2CH2CH3 3) CH3CH=CHCH=CHCCCH3 4) BrCH2CH2CCCH2CH3

    5) Draw acetylene 6) Draw (S)-5-phenyloct-2-yne 7) Draw hepta-3,6-dien-1-yne

    8) The carbon-carbon triple bond of an alkyne is composed of

    A) 3 s bonds B) 3 p bonds C) 2 s bonds and 1 p bond D) 1 s bond and 2 p bonds

    9) Why are terminal alkynes more acidic than other hydrocarbons?

    10) Provide the structure of the major organic product(s) in the reaction below.
    1) NaNH2
    CH3CH2C CH
    2) PhCH2Br
    11) Which of the species below is less basic than acetylide?

    A) CH3Li
    B) CH3ONa
    C) CH3MgBr
    D) both A and C
    E) all of the above

    12) Describe a chemical test for distinguishing terminal alkynes from internal ones.

    13) 2-Methylhex-3-yne can be prepared by the reaction of an alkynide with an alkyl halide. Does the better
    synthesis involve alkynide attack on bromoethane or on 2-bromopropane? Explain your reasoning.

    14) Provide the structure of the major organic product(s) in the reaction below.

    C C Na + Br

    15) Provide the structure of the major organic product(s) in the reaction below.

    O
    +
    NaNH2 H3O
    C CH

    16) Provide the structure of the major organic product(s) in the reaction below.

    H2

    Lindlar's
    catalyst

    17) Provide the structure of the major organic product(s) in the reaction below.

    Na
    CH3CH2 C C CH3
    NH3
    18) Provide the structure of the major organic product(s) in the reaction below.

    HBr (1 equivalent)
    C CH

    19) Provide the structure of the major organic product(s) in the reaction below.

    HgSO4
    C CH
    H2SO4, H2O

    20) Provide the structure of the major organic product(s) in the reaction sequence below.

    Sia2BH H2O2
    C CH
    -
    OH

    21) Provide the structure of the major organic product(s) in the reaction below.
    1) O3

    2) H2O

    22) To a solution of propyne in diethyl ether, one molar equivalent of CH3Li was added and the resulting
    mixture was stirred for 0.5 hour. After this time, an excess of D2O was added. Describe the major organic
    product(s) of this reaction.
    A) CH3CCD + CH4
    B) CH3CCCH3
    C) CD3CCD3
    D) CH3CCCD3
    E) CH3CCD + CH3D

    23) Provide the structure of the major organic product(s) in the reaction below.

    D2
    Ph Ph
    Pd / BaSO4 / quinoline

    24) Which of the alkyne addition reactions below involve(s) an enol intermediate?

    A) hydroboration/oxidation
    B) treatment with HgSO4 in dilute H2SO4
    C) hydrogenation
    D) both A and B
    E) none of the above

    25) Draw the products which result when oct-3-yne is heated in basic potassium permanganate solution.

    QUESTIONS 26-33 INVOLVE MULTISTEP SYNTHESES. PROVIDE THE STEPS BY WHICH THE
    PRODUCT GIVEN CAN BE PREPARED FROM THE STARTING MATERIAL GIVEN.

    26) Prepare racemic 2,3-dibromobutane from propyne 27) Prepare meso-2,3-dibromobutane from propyne

    28) Prepare hept-1-yne from hept=1-ene. 29) Prepare butylbenzene from phenylacetylene

    30) Prepare trans-pent-2-ene from propyne.


    31) Prepare the compound shown below from acetylene.

    OH

    32) Prepare the compound shown below from acetylene.

    H CH3
    H3C H
    O

    33) How many distinct alkynes exist with a molecular formula of C4H6?

    A) 0 B) 1 C) 2 D) 3 E) 4

    34) Name the compound which results when pent-2-yne is subjected to catalytic hydrogenation using a
    platinum catalyst.

    35) Which of the following reagents should be used to convert hex-3-yne to (E)-hex-3-ene?

    A) H2, Pt B) Na, NH3 C) H2, Lindlar's catalyst D) H2SO4, H2O E) HgSO4, H2O

    36) Which of the following reagents should be used to convert hex-3-yne to (Z)-hex-3-ene?

    A) H2, Pt B) Na, NH3 C) H2, Lindlar's catalyst D) H2SO4, H2O E) HgSO4, H2O

    37) Draw the product that results when CH3CCLi reacts with CH3CH2COCH2CH3 followed by addition of H2O

    38) Name the compound which results when pent-1-yne is treated with sodium in liquid ammonia.

    39) Explain why the synthetic route shown below would be unsuccessful.

    Br
    CH3CH2Br NaNH2
    HC C Na

    40) Explain why the synthetic route shown below would be unsuccessful.

    CH3CH2Br NaOCH3 CH3CH2Br


    HC C Na C C

    41) Provide the major organic product of the reaction shown below.

    Ph H +
    NaNH2 H3O
    C CH

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