1.

Using Woodward-Fieser's rule, calculate wavelengths of maximum UV absorption for

following compounds:

a)

b)

Base value:
alkyl
groups:

217 nm
3x5

c)

Base value:

15 nm

alkyl
groups:

253 nm
2x5

10 nm

calculated:

232 nm

calculated:

263 nm

observed:

234 nm

observed:

256 nm

d)
Base value:
alkyl groups or
ring residues:

e)
4x5

Exocyclic
double bond:

253 nm
20 nm

5 nm

calculated:

278 nm

observed:

275 nm

f)

Base value:
alkyl groups
or ring
residues:
Exocyclic
double
bond:
extra
conjugation:
calculated:
observed:

5x5

214 nm
25 nm

3x5

15 nm

1x30

30 nm
284 nm
283 nm

g)

Base value:

215 nm

-alkyl groups
or ring residues:

1x10

10 nm

-alkyl groups
or ring residues:

2x12

24 nm

calculated:
observed:

Base
value:
alkyl
groups:
Exocyclic
double
bond:
calculated:
observed:

249 nm
249 nm

Base value:
five
membered
ring parent
enone
-alkyl
groups or
ring
residues:
Exocyclic
double
bond:
calculated:
observed:

202 nm

2x12

24 nm

1x5

5 nm

231 nm
226 nm

214 nm
3x5

15 nm
5 nm

234 nm
235 nm

h)
Base value:
five
membered
ring parent
enone
-Br
-alkyl
groups or
ring
residues:
Exocyclic
double
bond:
calculated:
observed:

202 nm

2x12

25 nm
24 nm

1x5

5 nm

256 nm
251 nm