{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Dolbier HW Solutions 382 - Lithium dimethylcuprate...

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

View Full Document Right Arrow Icon
18.16 The enolate of dibenzyl ketone adds to methyl vinyl ketone in the conjugate addition step. via The intramolecular aldol condensation that gives the observed product is 18.17 A second solution to the synthesis of 4-methyl-2-octanone by conjugate addition of a lithium dialkylcuprate reagent to an , -unsaturated ketone is revealed by the disconnection shown: According to this disconnection, the methyl group is derived from lithium dimethylcuprate. 18.18 ( a ) In addition to the double bond of the carbonyl group, there must be a double bond elsewhere in the molecule in order to satisfy the molecular formula C 4 H 6 O (the problem states that the CH 3 CH 2 CH 2 CH 2 CH CHCCH 3 O O CH 3 CH 2 CH 2 CH 2 CHCH 2 CCH 3 LiCu(CH 3 ) 2 3-Octen-2-one
Image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Lithium dimethylcuprate 4-Methyl-2-octanone CH 3 CH 3 CH 2 CH 2 CH 2 CH CHCCH 3 O O CH 3 CH 2 CH 2 CH 2 CHCH 2 CCH 3 Disconnect this bond. CH 3 CH 3 b a 2 1,3-Diphenyl-2,6-heptanedione C C 6 H 5 CH 2 CHC 6 H 5 O O CH 2 CH 2 CH 3 C H 3 C C 6 H 5 C CHC 6 H 5 C O HO CH 2 CH 2 CH 3-Methyl-2,6-diphenyl-2-cyclohexen-1-one NaOCH 3 CH 3 OH 2 H 2 O C 6 H 5 C 6 H 5 O H 3 C C 6 H 5 CH 2 CCHC 6 H 5 H 2 C O O 2 CHCCH 3 C 6 H 5 CH 2 CCHC 6 H 5 2 O H 2 C O CHCCH 3 Methyl vinyl ketone 1,3-Diphenyl-2,6-heptanedione Dibenzyl ketone NaOCH 3 CH 3 OH C 6 H 5 CH 2 CCH 2 C 6 H 5 1 CHCCH 3 H 2 C O O C 6 H 5 CH 2 CCHC 6 H 5 CH 2 CH 2 CCH 3 O O 476 ENOLS AND ENOLATES...
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