Questions:

Assign which diastereoisomer the product is

3
JHaHb = 5.8 Hz

The coupling constant of vicinal hydrogen atoms Ha and Hb, is 5.8 Hz as calculated from
the ‘H NMR spectrum. According to the reference paper which shows:

anti. J1.2 = 6.8 Hz syn. J1.2 = 10.0 Hz

my product should be an anti - diastereoisomer

With reference to the karplus graph. The dihedral angle between Ha and Hb should be
around either 45° or 130°
where R1: MeOC6H4
45°
this is syn product

130° this is anti product

These elipsed conformation can be stabilized be hydrogen bonding between NO 2 group
NH group, as shown below:

The structure can be drawn into a chair – like conformation.

Syn: Anti:

Ha & Hb Ha & Hb
trans cis

However, Ha and Hb are antiperiplanar and they are in trans – position to each other in
Syn – product. The axial – axial trans coupling should be much larger than cis – coupling
(around 6.8 Hz). My product (3JHaHb = 5.8 Hz) is therefore an anti – product.