Organic Chemistry II Lessons

CHM 2211C Lesson 14: Dienes and Conjugated Systems gy

1. Draw a structure that satisfies each of the following statements.

a) an isolated cyclohexadiene b) a conjugated triene with six total carbons
¢) acumulated diene with a total of four carbons

a) b) c)


@ SN W SN—cm=c” cH 3

g Tw




2. Draw a structure that satisfies each of the following statements.

a) acumulated diene with a total of eight carbons b) an isolated pentadiene
c) aconjugated cyclododecatriene

a) b) c)




3. Draw a structure that satisfies each of the following statements.

a) acumulated nonadiene with the shortest chain possible b) a conjugated hexaene
c) an isolated cyclododecatriene L N bonds

a) b) c)



N\//\,//\//\// \

, 4. Provide the structures of all possible compounds that might be formed by the complete reaction of
2,4,6-trimethylocta-1,3,5-triene with water and sulfuric acid. Clearly label the structures expected to
be the kinetic and thermodynamic products of thi(g )rcaction.
H—oul
NG » 2 H,0
H,SO,



Pl — H




Vainekic -\'hermoéfl NnomMmic



5. Provide the structures of all possible compounds that might be formed by the complete reaction of
3,7-diethyl-5-methylnona-2,4,6-triene with hydrochloric acid. Clearly label the structures expected
to be the kinetic and thermodynamic products of this reaction.
|5 -Cg"
/)/\‘/)K HCl -




[




ainexsic THermodym
ovan ©


6. Provide the structures of all possible compounds that might be formed by the complete reaction of 7-
dimethylethyl-5-ethyl-3,6-dimethyldeca-3,5,7-triene with cyanogen bromide. Clearly label the
structures expected to be the kinetic and thermodynamic products of this reaction.


BrCN
/\;;/Q\/ ccl,

or &

NC. k. o e
/ =~ ~ / -~ -~


or D¢
B


Rineric Yhermodinamie