Unformatted text preview: 6 5 pts) Draw all of the monochlorination products (constitutional isomers) that would be formed in the
action below. 5
+0 (3de xiii
(5 pts) You are L/ktrying to determine the structure of an unknown compound A. A has a molecular formula of C14 4.111 order to determine the structure, you treated A with ozone followed by an acidic zinc work up. The products isolated aﬁer the ozonolysis are shown below. Based on the ozonolysis products, propose a
possible structure for A. A 1) 03, —78°c “(E
2) Zn, H20 + 03:60 C14H24 echanism: ' ,6 pts) Draw a detailed mechanism for the addition of HCl to 3 ,3-dimethyl-1-butene to give 2-chloro-2, 3- ethylbutane and 2-chloro- 3 ,3-dimethy1butane. Use arrows to show electron motion. Be sure to indicate
any atoms that have formal charges. H33 CH3 CH
H39 HG! ‘33 CH3 H38
FGHz mm rise—H chXw/CHE
H CHgﬁHs C,
H33 CH3 H56 CH3 7 wbw K ‘
”35 \ H343 ‘ ’“7 ”334:3
CH H"CI W t m '
HF\:_,) + CH5 2’1} CH3 H38} Vet-13 ”35 "i'_§"'
Ci CH3 CH3 ...
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