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    Alkyne Exercises

    Uploaded by

    04Andhika Fathurrohman
    This document contains exercises and questions to accompany a textbook on organic chemistry. It covers topics related to alkynes including naming alkynes, drawing alkynes, reactions of alkynes such as addition, hydration, reduction and oxidation. It also discusses the acidity of alkynes and formation of acetylide anions. Questions provide examples of alkynes and ask students to propose reaction schemes and syntheses starting from various alkynes. The solutions then show the step-by-step workings and products.

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    © All Rights Reserved
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    Alkyne Exercises

    Uploaded by

    04Andhika Fathurrohman
    66 views10 pages
    This document contains exercises and questions to accompany a textbook on organic chemistry. It covers topics related to alkynes including naming alkynes, drawing alkynes, reactions of alkynes such as addition, hydration, reduction and oxidation. It also discusses the acidity of alkynes and formation of acetylide anions. Questions provide examples of alkynes and ask students to propose reaction schemes and syntheses starting from various alkynes. The solutions then show the step-by-step workings and products.

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    This document contains exercises and questions to accompany a textbook on organic chemistry. It covers topics related to alkynes including naming alkynes, drawing alkynes, reactions of alkynes such as addition, hydration, reduction and oxidation. It also discusses the acidity of alkynes and formation of acetylide anions. Questions provide examples of alkynes and ask students to propose reaction schemes and syntheses starting from various alkynes. The solutions then show the step-by-step workings and products.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    66 views10 pages

    Alkyne Exercises

    Uploaded by

    04Andhika Fathurrohman
    This document contains exercises and questions to accompany a textbook on organic chemistry. It covers topics related to alkynes including naming alkynes, drawing alkynes, reactions of alkynes such as addition, hydration, reduction and oxidation. It also discusses the acidity of alkynes and formation of acetylide anions. Questions provide examples of alkynes and ask students to propose reaction schemes and syntheses starting from various alkynes. The solutions then show the step-by-step workings and products.

    Copyright:

    © All Rights Reserved
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    of 10

    9.

    E: Alkynes: An Introduction to Organic


    Synthesis (Exercises)
    1.
    2. Last updated
    Jul 5, 2020
    3.
    o 8.E: Alkenes: Reactions and Synthesis (Exercises)
     
    o 10.E: Organohalides (Exercises)
    4. picture_as_pdf
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    These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry
    textbook.

    9.0 Unit Preview


    9.1 Naming Alkynes
    9.1 Exercises

    Questions

    Q9.1.1

    Name the following compounds:


    Q9.1.2

    How many isomers are possible for C5H8? Draw them.

    Q9.1.3

    Draw the following compounds:

    A) 4,4-dimethyl-2-pentyne

    B) 3-octyne

    C) 3-methyl-1-hexyne

    D) trans 3-hepten-1-yne

    Q9.1.4

    Do alkynes show cis-trans isomerism? Explain.

    Solutions

    S9.1.1

    A – 3,6-diethyl-4-octyne

    B – 3-methylbutyne

    C – 4-ethyl-2-heptyne
    D – cyclodecyne

    S9.1.2

    2 possible isomers

    S9.1.3

    S9.1.4

    No. A triply bonded carbon atom can form only one other bond and has linear electron geometry
    so there are no "sides". Allkenes have two groups attached to each inyl carbon with a trigonal
    planar electron geometry that creates the possibility of cis-trans isomerism.

    9.2 Preparation of Alkynes: Elimination Reactions


    of Dihalides
    9.3 Reactions of Alkynes: Addition of HX and X2X2
    9.4 Hydration of Alkynes
    9.4 Exercises

    Questions

    Q9.4.1
    What alkyne would you start with to gain the following products, in an oxidation reaction? Keep
    in mind resonance.

    Q9.4.2

    Propose a reaction scheme for the following compound starting from the alkyne and showing
    required reagents and intermediates.

    Solutions

    S9.4.1
    S9.4.2

    9.5 Reduction of Alkynes


    9.5 Exercises

    Questions

    Q9.5.1

    Usng any alkyne how would you prepare the following compounds:

    pentane, trans-4-methyl-2-pentene, cis-4-methyl-2-pentene.

    Solutions

    S9.5.1

    9.6 Oxidative Cleavage of Alkynes


    9.7 Alkyne Acidity: Formation of Acetylide Anions
    9.7 Exercises

    Questions

    Q9.7.1
    If OH- has a pKa of 14.00 in water, what pKa be required to deprotonate OH-?

    Solutions

    S9.7.1

    Need a stronger base, or a compound with a pKa > 14.00 to deprotonate.

    9.8 Alkylation of Acetylide Anions


    9.8 Exercises

    Questions

    Q9.8.1

    Give the possible reactants for the following formations:

    Q9.8.2

    Propose a synthetic route to produce 2-pentene from propyne and an alkyl halide.

    Solutions

    S9.8.1
    S9.8.2

    9.9 An Introduction to Organic Synthesis


    9.9 Exercises

    Questions
    Q9.9.1

    Starting at 3-hexyne predict synthetic routes to achieve:

    A – cis-3-hexene

    B – 3,4-dibromohexane

    C – 3-hexanol

    Q9.9.2

    Starting with acetylene and any alkyl halides propose a synthesis to make (a) pentanal and (b)
    hexane.

    Solutions

    S9.9.1

    S9.9.2

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