CHE 331-800 12.3 - 4 Le Lewué 94595[gig/W Benzylic...

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

View Full Document Right Arrow Icon
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
Image of page 2
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.

Unformatted text preview: 4/ Le Lewué 94595 [gig/W // Benzylic Substitution and Benzylic Radicals An atom or group bonded to an sp3-hybridized carbon adjacent to a benzene ring is called a benzylic group. The group is said to be bonded at the benzylic position CH3 O + N—Br O Methylbenzene NBS O + N—H O (Toluene) Benzyl bromide (-bromoto|uene) ’1‘ (64%) d, 11/24/14 14 f \“flcvg Cl (161616.61 I' I (oi ll ago to (551)215ML Qigviij , L911“ 5 9 6* <16: IS 1% gum/rqflwfl/g W cm a cow ‘4" a (i (l m 0% @ t5 2 ;> —"‘:——> heat heat or light or light Benzyl Dichloromethyl Trichloromethyl chloride benzene benzene omOLAOK gonJrrkloxo/ beowacz (benzevu (10% 'im’VQC/‘V, X2 ._—..> Benzyllc radical (more stable) 1-Halo-1-phenylethane (major product) Chico" 1° Radical (less stable) 1-Halo-2-phenylethane (minor product) 11/24/14 15 O Radical Addition to Alkenes: The anti- Markovnikov Addition of Hydrogen Bromide anti-Markovnikov addition. 00 i-Bromopropane CHJCH=CH2 + HBr i» CI~i_,(|:HCH3 peroxides Br 2-Bromopropane Mechanism: Chapter 10 O Radical Polymerization of Alkenes: Chain-Growth Polymers I) Polymers are macromolecules made up of repeating monomer subunits. I) Addition of hydrogen bromide In the presence of peroxides gives R R CHJCH=CH2 + Hllr -———* CHJCHZCH2Br Anti»Markovnik0v addition Murkovnikov addition 31 lb Polyethylene is made of repeating subunits derived from ethylene I. \lnimmt‘rit' unitsx l ' r ' ,Ll' J V l‘ m CH3=CH3 —CH3CH2+CH3CH3->;CHZCH2— Ethylene Polyethylene monomer polymer in: and u are large numbers) It Polystyrene is made in an analogous reaction using styrene as the monomer. m CH2=CH ""‘Ymmm‘m‘ —CH3CH +CH2CH T CHECH ~— Styrene Polystyrene 32 11/24/14 16 F 5r“: 7(ér ‘I‘ “D , ’ 9H2 ‘ \ 3C7 ff ...
View Full 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