pset2_key (1) - in both cases. a. 3-buten-1-ol...

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

View Full Document Right Arrow Icon
1. (self-explanatory) 2. a. Starting materials: 1-bromopropane, PPh3, then nBuLi/THF (or NaHMDS/ether or toluene which actually gives higher cis selectivity (fyi)) then pentanal. OR: 1- bromopentane and propanal, etc. b. trans-3-octene c. 1 H NMR coupling constants (Jcis=6-12 and Jtrans=12-18) d. Lindlar reduction of 3-octyne and Li/NH3 reduction of 3-octyne. Compare NMR spectra to that/those obtained for Wittig product(s). 3. 4-(para-nitrophenyl)-1-butanol. 4. 2-cyclohexenone (conjugated). The M-28 in the MS is loss of C=O. 5. C4 H8 O
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: in both cases. a. 3-buten-1-ol (CH2=CH-CH2-CH2-OH, the 5.0- 6.0 ppm pattern is typical for a terminal alkene attached to a CH2.) b. 1-buten-3-ol (CH2=CH-CH(OH)-CH3, the 5.0- 6.0 ppm pattern is typical for a terminal alkene attached to a CH. Hard to see, but 5.9 ppm peak is a ddd, and the other 2 alkenes are geminal, exhibiting only cis and trans and trans coupling to the alkenyl CH.) 1...
View Full Document

This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

Ask a homework question - tutors are online