Skip to main content
Chemistry LibreTexts

17.6: Reaction Examples

  • Page ID
    216692
  • SOLVED PROBLEM 8-1, p. 329

    clipboard_e8d5e3405e59eec9e6f658b810e9ef3b3.png

    Analysis: Markovnikov addition of HBr to the C=C bond. Use HBr:

    clipboard_e5a8dd73be888206c246e3fa9f099c3b5.png

    Complement:

    clipboard_e920c6b9fd96b3a15ce4c204627c6e794.png

    Analysis: Anti-Markovnikov addition of HBr to the C=C bond. Use HBr in the presence of peroxides

    clipboard_e3de94aceb6093355fb4a875212fd3006.png

    Retrosynthetic analysis, or retrosynthesis:

    clipboard_e12036b792131fd34fa5ca812c28332d5.png

    Recommended problem: 8-4, p. 330

    OXYMERCURATION - DEMERCURATION, ALSO CALLED OXYMERCURATION - REDUCTION

    clipboard_ec49885c369481222e5ec9fecdf51f049.pngMarkovnikov alcohol

    clipboard_eaea3d47d8d18321c20a57864c034727b.pngMarkovnikov alcohol without rearrangement

    Contrast with addition of water in the presence of strong acid:

    clipboard_e01a429238043c7df99e3ac9b42b5eb62.png

    clipboard_ea4bd39006617484a0ab14dbdb4f32c06.png

    HYDROBORATION - OXIDATION SEQUENCE.

    An effective way to make Anti-Markovnikov alcohols. Water adds to the double bond with syn-stereochemistry.

    clipboard_e70c37d842d987fe1edd7b549c1b82d08.pngAnti-Markovnikov alcohol

    SOLVED PROBLEM 8-3, p. 339

    clipboard_e252849062090b5e57d1780564accaf7c.png

    Problem 8-15 (b)

    clipboard_e45a866c4b70a3a6e71f4fc597f656a52.png

    Can I make B from A by hydroboration - oxidation?

    clipboard_eb68a814e31b2c3e5b4edbb4519c393f3.pngNotice that the methyl and the alcohol group are cis to each other.

     

    Analysis:

    clipboard_e91574b77739f95f9cd8211af8bb9c8df.png

    Answer: NO

    Recommended: 8-15 (c), p. 342

     

    ADDITION OF CHLORINE OR BROMINE TO THE C=C BOND

    clipboard_e342ac3611e59b0241ff05790e4dd5fbd.png

    Anti addition yields the trans product, which is chiral. Therefore the enantiomer also forms.

    clipboard_e33c4c41403d11bd87a6d3867b31b4b7a.png

    clipboard_ece24cb7d5e0af14d8757a154ece9ebc5.png

    clipboard_e5ee2e175ad0416b35de8a1504a6aef6a.png

    Recommended: 8-17, p. 345

    Variation with water:

    clipboard_e9dda38396cfce5433144fc6b47f5bba4.png

    Recommended: 8-5 and 8-6, p. 347​​​​​​​

     

    CATALYTIC HYDROGENATION - Transformation of alkenes into alkanes (syn addition of hydrogen).​​​​​​​

    clipboard_e49c372439021596bdf43be403b6a7e0f.png

    Recommended: 8-23, p. 350

     

    SYN HYDROXYLATION - Syn addition of OH / OH to the C=C bond.

    clipboard_eeb24483b68c955dbc200af595e0966e0.png

    ANTI HYDROXYLATION SEQUENCE- Anti addition of OH / OH to the C=C bond.

    clipboard_ef2b963269b9e9cfe3f1b6459a6fd701c.png

    clipboard_e28015f1fcfabec89727f06bed66c039a.png

    clipboard_e6cf23381d5f2afe50541dd00746c40c5.png

    clipboard_e8ddd0a1b3a92cf87b8e78ddab1345ad6.png

    Recommended for syn and anti hydroxilation: 8-34 (all), p. 359

     

    OXIDATIVE CLEAVAGE: Strong oxidation with potassium permanganate.

    In this reaction each of the sp2 carbons involved in the pi bond gets oxidized to its maximum possible oxidation state. Refer to notes set # 20 (Oxidation and Reduction in Organic Chemistry) to find out what these states are.

    clipboard_e1a256ebdbe7524788ff55118cd490ed6.png

    OXIDATIVE CLEAVAGE: Ozonolysis

    In this reaction each of the sp2 carbons involved in the pi bond gets oxidized either to aldehyde or ketone, depending on whether it ends up at the end of a carbon chain or in the middle after the pi bond cleaves. If the oxidized carbon ends up at the end of a carbon chain it becomes an aldehyde, otherwise it becomes a ketone.

    clipboard_e3238caf25c3e08765aaca486b11bc79b.png

    Recommended strong oxidation (oxidative cleavage) with KMnO4 and with ozone: 8-7, 8-36, and 8-37, p. 362-363.

    Recommended problems from the end of the chapter: 47 (all), 49 ( a-f ), 58 (all), 63

    • Was this article helpful?