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Reactions of Chapter 12 (Continued)

8/11/2019

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Reaction #7: Addition of carbene (:CR2) ​to form a cyclopropane (Could not find a suitable video for cyclopropane synthesis)
Picture

 Reaction #8: Halogenation-- addition of Br2, Cl2, with or without a protic solvent 
-Forms two adjacent anti-halogens in aprotic solvent.
-Forms two adjacent anti- halogen + solvent in protic solvent (ROH or H2O)
Note: the opening of the halonium ion (halogen ring) can occur not just with H2O, but with other alcohols (ROH)

Reaction 9: Epoxidation by peroxycarboxylic acid
-Forms an epoxide
This reaction forms an epoxide. This is a good time to review epoxide ring opening from 118A: https://ericpdotutoring.weebly.com/week-six 

Note for synthesis: Opening epoxides with NaOH or H+, H2O will form two alcohols anti to one another. This is in contrast to the next reaction, reaction 10- KMnO4 or OsO4, which forms syn diols (2 alcohols). 

Reaction 10: Dihydroxylation by KMnO4 or OsO4
-Forms two adjacent, syn- alcohols
Picture
Note: Nasiri teaches different reagents than what is shown in the video. Conceptually and mechanistically, the video is still helpful. 
Also:
we did not cover the last reaction shown: cleavage of alkenes (beginning 9:45~ onwards)
Instead: 
We learned Ozonolysis for cleavage of alkenes
*Feel free to use reactions that Nasiri did not teach on synthesis questions on exams*

Reaction 11: Ozonolysis
-
Cleaves alkenes and replaces them with carbonyls
Picture
Note: Khan Academy uses DMS as their second step. DMS = dimethyl Sulfide = CH3SCH3
Note: The first step of Ozonolysis's mechanism is very similar to reaction 10 with KMnO4/ OsO4
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  • Home
  • Courses
    • Organic Chemistry Che118A (Fall 2021) >
      • Che 118A Table of Contents
      • Che118A Introduction
      • Week One
      • Week Two
      • Week Three
      • Week Four
      • Week Five
      • Week Six
      • Spectroscopy Resources
      • Reactions after MT2
    • Organic Chemistry Che118B (Summer Session) >
      • Che 118B Table of Contents
      • Che118B Introduction
      • Reaction Summaries
      • Week One
      • Week Two
      • Week Three >
        • Lectures (Ch 14-15)
        • Practice Questions
      • Week Four >
        • Lectures (Ch 15-16)
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    • Organic Chemistry Che118C (Quarter-based) >
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        • Chapter 19 (MT 1 part 1)
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