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    Chem 223 SI - Chapter 19 Part 2

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    Yvonne Chueh
    1) The document provides an overview of reactions of alkynes, including halogenation, hydrohalogenation, hydration, oxidation, and ozonolysis. 2) Specific reactions are discussed, such as addition of HX to alkynes and the products formed from mercuric ion-catalyzed versus hydroboration-oxidation hydration of alkynes. 3) Key similarities and differences are highlighted between reactions of alkenes and alkynes, such as product orientation and final products formed.

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    Chem 223 SI - Chapter 19 Part 2

    Uploaded by

    Yvonne Chueh
    95 views5 pages
    1) The document provides an overview of reactions of alkynes, including halogenation, hydrohalogenation, hydration, oxidation, and ozonolysis. 2) Specific reactions are discussed, such as addition of HX to alkynes and the products formed from mercuric ion-catalyzed versus hydroboration-oxidation hydration of alkynes. 3) Key similarities and differences are highlighted between reactions of alkenes and alkynes, such as product orientation and final products formed.

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    1) The document provides an overview of reactions of alkynes, including halogenation, hydrohalogenation, hydration, oxidation, and ozonolysis. 2) Specific reactions are discussed, such as addition of HX to alkynes and the products formed from mercuric ion-catalyzed versus hydroboration-oxidation hydration of alkynes. 3) Key similarities and differences are highlighted between reactions of alkenes and alkynes, such as product orientation and final products formed.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    95 views5 pages

    Chem 223 SI - Chapter 19 Part 2

    Uploaded by

    Yvonne Chueh
    1) The document provides an overview of reactions of alkynes, including halogenation, hydrohalogenation, hydration, oxidation, and ozonolysis. 2) Specific reactions are discussed, such as addition of HX to alkynes and the products formed from mercuric ion-catalyzed versus hydroboration-oxidation hydration of alkynes. 3) Key similarities and differences are highlighted between reactions of alkenes and alkynes, such as product orientation and final products formed.

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    Chem 223 SI 04.10.

    13 Chapter 9 Part 2: Alkynes Chapter 9 Review: 1) Draw an acceptable structure for hepta-1,4-diene-6-yne

    2) Briefly explain why the synthetic route shown below would be unsuccessful.

    3) Provide the major organic compound of the reaction shown below.

    4) Complete the following reaction sequences below by filling in the missing reagents or structures.

    5) Using acetylene and any other reagents, synthesize: a) 5-methyl-2-hexyne

    b) cyclodecyne

    c)

    Halogenation of Alkynes Add bromine or chlorine to alkynes Add one mole X2 to alkyne, stereochemistry will be either ________ or ________ o This product is a _______________________ o Difficult to stop here If a second mole of X2 is added, the _____________________________ results
    Cl2

    Hydrohalogenation of Alkynes Addition of HX Similar to addition of hydrogen halides to double bonds! Addition to terminal alkynes: o Add one mole of HX to produce _______________________ Orientation of this addition? (Hint: stability of the reactive intermediate!) o Add another mole of HX to produce _________________________ What is the orientation of this addition? (Same hint)

    Step 1:

    Addition to internal alkynes o Mixture of products (E and Z isomers) Steps of HX addition to alkyne (Hint: very similar to HX addition to alkenes!)

    Step 2:

    Step 3:

    Step 4:

    How would radical addition of HBr affect the addition across the triple bond?

    HBr

    Hydration of Alkynes to Ketones and Aldehydes 1) Mercuric Ion Catalyzed Hydration o Acid-catalyzed addition of H2O What are we expecting to happen in the reaction when we see acidcatalyzed? Mercuric sulfate in aqueous sulfuric acid Adds water to form the ________, which then undergoes acid-catalyzed tautomerism to produce to _________ form

    HgSO4 H2SO4, H2O

    Acid-Catalyzed Keto-Enol Tautomerism Mechanism:

    o o

    Similarities with alkene reaction: ______________________________ orientation is observed Differences with the alkene reaction: What is formed rather than the mercuric ring? ________________________ What is the final product, rather than an alcohol and why? How is the last step different? Different reagents, what are they here vs. for alkene?

    2) Hydroboration Oxidation o How do we prevent the addition of two molecules of borane?

    o o

    Similarities with the alkene reaction: ___________________________ orientation is observed Same oxidation reagents are used: ________, ____________, __________ Differences with the alkene reaction: What is the final product, rather than a vinyl alcohol?

    Sia2BH

    Base-Catalyzed Keto-Enol Tautomerism Mechanism

    Oxidation of Alkynes Permanganate Oxidations o Conceptually the same as alkene oxidation Like hydroxyating each pi bond, then losing 2 H2O o Mild conditions (cold, dilute, neutral) of KMnO4 forms __________________

    KMnO4 cold, dilute

    What about terminal alkynes? The diketone compound we saw above is further oxidized

    Warm, basic KMnO4 causes oxidative cleavage (further oxidizes) Internal alkynes yield ______________________________ How do you convert to acid? Terminal alkynes yield _______________________ and ______________________

    Ozonolysis o Conceptually similar to ozonoylsis of alkenes Ozonoylsis of triple bonds yields ________________________ Terminal alkynes yield _____________________

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