{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Dolbier HW Solutions 515 - m-nitroaniline by any of a...

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

View Full Document Right Arrow Icon
( d ) The conversion of p -chloronitrobenzene to p -chloroaniline was cited as an example in the text to illustrate reduction of aromatic nitro compounds to arylamines. p -Chloronitrobenzene is prepared by nitration of chlorobenzene. The para isomer accounts for 69% of the product in this reaction (30% is ortho, 1% meta). Separation of p -chloronitrobenzene and its reduction completes the synthesis. Chlorination of nitrobenzene would not be a suitable route to the required intermediate, because it would produce mainly m -chloronitrobenzene. ( e ) The synthesis of m -aminoacetophenone may be carried out by the scheme shown: The acetyl group is attached to the ring by Friedel Crafts acylation. It is a meta director, and its nitration gives the proper orientation of substituents. The order of the fi rst two steps cannot be reversed, because Friedel Crafts acylation of nitrobenzene is not possible (Section 12.16). Once prepared,
Image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: m-nitroaniline by any of a number of reagents. Indeed, all three reducing combinations described in the text have been employed for this transformation. Yield Reducing agent (%) m-Nitroacetophenone H 2 , Pt 94 ↓ Fe, HCl 84 m-Aminoacetophenone Sn, HCl 82 22.12 ( b ) Dibenzylamine is a secondary amine and can be prepared by reductive amination of benz-aldehyde with benzylamine. H 2 , Ni C 6 H 5 CH O C 6 H 5 CH 2 NH 2 C 6 H 5 CH 2 NHCH 2 C 6 H 5 1 Dibenzylamine Benzylamine Benzaldehyde Benzene HNO 3 H 2 SO 4 reduce AlCl 3 CH 3 CCl O Acetophenone CCH 3 O m-Nitroacetophenone NO 2 CCH 3 O m-Aminoacetophenone NH 2 CCH 3 O p-Chloroaniline Cl NH 2 p-Chloronitrobenzene Cl NO 2 1. Fe, HCl; 2. HO 2 or 1. Sn, HCl; 2. HO 2 H 2 , catalyst; or Benzene Chlorobenzene Cl o-Chloronitrobenzene NO 2 Cl p-Chloronitrobenzene Cl NO 2 Cl 2 FeCl 3 HNO 3 H 2 SO 4 1 AMINES 609...
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