{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Solutions_Manual_for_Organic_Chemistry_6th_Ed 108

Solutions_Manual_for_Organic_Chemistry_6th_Ed 108 - ǽ...

Info icon This preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
6-9 continued The resonance-stabilized allylic radical intermediate has radical character on both the 1 ° and carbons, so bromine can bond to either of these carbons producing two isomeric products. (b) Allylic bromination of cyclohexene gives 3-bromocyclohex-l-ene regardless of whether there is an allylic shift. Either pathway leads to the same product. If one of the ring carbons were somehow marked or labeled, then the two products can be distinguished. (We will see in following chapters how labeling is done experimentally.) 6- 10 (a) (b) o NBS CH3 I CH3 -C-CH3 I hv CH3 o- Br + y Br CH3 I CH3-C -CH2CI I CH3 the second structure from an allylic shift is identical to the first structure-only one compound is produced This compound has only one type of hydrogen-only one monochlorine isomer can be produced.
Image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: ǽ CÅ2C½¾ hV C½¾Æ Æ Br C½2C½¾ Bromination has a strong preference for abstract±Èg hydrogenÉ (Like 3°) that give stable rad±cal intermed±atesµ hV (or ÊB¼) Bromine atom wiLl abstract the hydrogeÈ giving the most stable radical; in this caseË the radical intermediate will be stabilized by resonance with the benzeÈe Ìing. Br (d) C hV ± + the second strUctUre from an allylic shift is IdentiCaL to the first strUctureÍOnly one coMpoUnd is prodUced (or NB¼) Br BromiÈe atom will abstract the hyDrogen giving the most Îtable radicalÏ iÁ this caseË the radical intermedÐate will be stabilized by resonance with the benzene ring. 6Ñ 1 1 (a) s¶bstitutionÃBr ±s replaced (b) eL±Ò±nationý and ÓÔ are lost ÕcÖ e×´m´nØÙ´ÚÛÃbÚÙ¹ Ür aÙÝms are ÞÚSt 6Ñ 1ß (a) C½¾(C½à)4C½2 á ÓC½2C½â (b) Cž(C½2)4C½2 ã äÊ 101...
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