{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Ch7slides - Chapter 7 Alkenes Reactions and Synthesis H C C...

Info icon This preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
1 Chapter 7: Alkenes: Reactions and Synthesis C C C C OH H C C H H C C OH X C C X X alcohol alkane halohydrin 1,2-dihalide C C X H halide alkene C C OH HO 1,2-diol C C halide C C O carbonyl C C alkene X Y + C C Y X Elimination Addition Electrophilic Addition Dehydrohalogenation: loss of HX from an alkyl halide to form an alkene + HBr Br H H H H H ether Br H H H + KOH EtOH (ethanol) H H + KBr + H 2 O
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
2 Hydration: addition of water (H-OH) across a double bond to give an alcohol Dehydration: Loss of water (H-OH) from an alcohol to give an alkene + H 2 O OH H H H H H H + OH H H H H H + H 2 O H + Addition of Halogens (X 2 ) to Alkenes: 1,2-dihalides C C C C X X 1,2-dihalide alkene X 2 1,2-dibromide has the anti stereochemistry Bromonium ion intermediate controls the stereochemistry + Br 2 Br Br + Br Br not observed
Image of page 2
3 Halohydrin Formation C C C C OH X halohydrin alkene "X-OH" X OH anti stereochemistry Br 2 , H 2 O + HBr Organic molecules are sparingly soluble in water as solvent. The reaction is often done in a mix of organic solvent and water using N-bromosuccinimide (NBS) as the electrophilic bromine source. DMSO, H 2 O N O O Br + Br OH N O O H + Note that the aryl ring does not react!!! For unsymmterical alkenes, halohydrin formation is Markovnikov-like in that the orientation of the addition of
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
This is the end of the preview. Sign up to access the rest of the document.

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern