Chapter 3: 36P (page 189)
Draw the structure that corresponds with each name.
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(k)
(l)
Short Answer
a)

b)

c)

d)

e)

f)

g)

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Chapter 3: 36P (page 189)
Draw the structure that corresponds with each name.
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(k)
(l)
a)

b)

c)

d)

e)

f)

g)

h)

i)

j)

k)

l)

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Draw the structure and give the molecular formula for each of the following compounds.
(a) 1-ethyl-3-methylcycloheptane
(b) isobutylcyclohexane
(c) cyclopropylcyclopentane
(d) 3-ethyl-1,1-dimethylcyclohexane
(e) 3-ethyl-2,4-dimethylhexane
(f) 1,1-diethyl-4-(3,3-dimethylbutyl)cyclohexane
Question: This is a Newman projection of a substituted cyclohexane.
(a) Draw the equivalent chair form
(b)Draw the equivalent structure using wedge and dash notation on a cyclohexane hexagon.
(c) Give the IUPAC name.

Question: Conformational studies on ethane-1,2-diol (HOCH2 -CH2OHhave shown the most stable conformation about the central C-Cbond to be the gauche conformation, which is 9.6 KJ/mol (2.3 kcal/mol)more stable than the anti-conformation. Draw Newman projections of these conformers, and explain this curious result.
In each pair of compounds, which compound has the higher boiling point? Explain your reasoning.
(a) Nonane or 3-methylheptane
(b) Octane or 2,3,4-trimethylpentane
(c) 2,3,5-trimethylhexane or nonane
Write structures for a homologous series of alkyl chlorides having from one to six carbons.
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