CH 310N POW-5_key - Br 2 CH 3 Br Br NaNH 2 Mixture of diastereomers CH 3 H 2 Lindlar CH 3 mCPBA CH 3 O Racemic CH 310N_POW-5 Williams Fall 2010 Due

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

View Full Document Right Arrow Icon
CH 310N_POW-5 Williams Fall 2010 Due Date: 8 AM, THURS, 10/07/10 1 Name (print): ___________________________________________________________ Signature: ______________________________________________________________ Do Homework in PEN! Please write the first three letters of your last name in the boxes
Background image of page 1

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

View Full DocumentRight Arrow Icon
CH 310N_POW-5 Williams Fall 2010 Due Date: 8 AM, THURS, 10/07/10 2 1. Synthesize the following product using only benzoic acid and propane as your source for carbon atoms. This is a long one! [ Hint : You should be able to do it in a TOTAL of twelve steps (arrows)or less]. Whenever a racemic or other product mixture is formed, only draw one isomer and indicate this by writing “racemic”, “E/Z mixture”, “mixture of diastereomers”. (4 pts) OH O H 3 C CH 3 CH 3 O racemic OH O 1) LiAlH 4 2) H 3 O OH PCC O 1 H 3 C CH 3 Br 2 , h ν H 3 C CH 3 Br t -BuOK E 2 H 3 C CH 2 1) BH 3 2) H 2 O 2 , NaOH H 3 C OH PBr 3 H 3 C Br Mg 0 Et 2 O H 3 C MgBr 1 1) 2) H 3 O, Heat CH 3 E/Z mixture
Background image of page 2
Background image of page 3

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

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Br 2 CH 3 Br Br NaNH 2 Mixture of diastereomers CH 3 H 2 , Lindlar CH 3 mCPBA CH 3 O Racemic CH 310N_POW-5 Williams Fall 2010 Due Date: 8 AM, THURS, 10/07/10 3 2. Predict the products. Where appropriate, list “racemic.” (2 pts) OMe OH 1) H 2 Cr 2 O 7 2) CH 2 N 2 O O OH 1) PDC 2) H 2 SO 4 , H 2 O 3) Heat 4) Br 2 , H 3 CCOOH OH 1) SOCl 2 2) Mg , Et 2 O 3) CO 2 , then H 3 O + 4) TsOH,-H 2 O HO CH 3 this goes along with step 4 MgBr 1) Acetaldehyde 2) PBr 3 3) Mg , Et 2 O 4) CO 2 , then H 3 O + 5) SOCl 2 Br O OMe OMe O O O CH 3 O Cl RACEMIC CH 310N_POW-5 Williams Fall 2010 Due Date: 8 AM, THURS, 10/07/10 4 3. Mechanism in a box: Fischer Esterification. Draw all arrows to indicate electron flow and include the correct structure in each box for the Fischer esterification. Include all lone pairs and charges!...
View Full Document

This note was uploaded on 01/12/2011 for the course CH 318N CH 318N taught by Professor Williams during the Spring '10 term at UT Arlington.

Page1 / 4

CH 310N POW-5_key - Br 2 CH 3 Br Br NaNH 2 Mixture of diastereomers CH 3 H 2 Lindlar CH 3 mCPBA CH 3 O Racemic CH 310N_POW-5 Williams Fall 2010 Due

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online