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Unformatted text preview: Practice
exam
2
answer
key
 
 1.
 Give
the
systematic
name
for
each
of
the
following
chemicals:
 
 a) b) c) Br d) O I F Cl (E)-3-methylhex-2-ene (E)-3-methoxy-4-methylhex-3-ene (Z)-1-bromo-1-iodo-2-methylbut-1-ene (Z)-2-chloro-3fluorobut-2-ene 2.
 Draw
the
following
molecules:
 a)
(E)‐1‐bromo‐2‐methyl‐2‐butene
 b)
3‐chloro‐1,4‐cyclohexadiene
 c)
1‐bromo‐4‐methyl‐2‐pentyne
 d)
(2E,4Z)‐2,4‐dichloro‐2,4‐heptadiene
 e)
(E)‐3‐iodo‐2‐pentene
 Cl 
 a) Br b) Br d) Cl e) Cl 
 3.
 Circle
the
more
stable
alkene.
 I 
 a) or b) or c) or 
 
 4.
 Draw
curved
arrows
to
show
the
flow
of
electrons
responsible
for
the
formation
of
 the
products
shown.
 H C H C H H H H O H H H H C C I H H H O H I H C H H C H H H C C I H + H I + H2O H H + H O H 
 5.
 Draw
the
two‐step
mechanism
with
curved
arrows
to
show
the
reaction
between
 cyclohexane
and
HBr.
 
 H Br H Br + H Br 
 
 
 6.
 Indicate
the
hybridization
and
ideal
bond
angles
for
the
following
atoms
in
the
 boxes
provided:
 sp3 <109.5o s p2 120o sp3 <109.5o s p 3 1 0 9 .5 o O HN O O P O O O O O OH P O O HO OH OH O N OH sp2 120o HO s p 3 < 1 0 9 .5 o 7.
 
Label
each
as
a
nucleophile
or
electrophile.
 H O H 
 F nuc . H O H H nuc . nuc. elect. nuc . elect. elect. 
 
 8.
 Draw
the
expected
product(s)
or
label
as
“NR”
if
no
reaction
would
be
expected
to
 occur
for
the
following:
 Cl + Cl OH + O H + H C OH CH O + H + HBr H Cl H Br + HCl + O H NR 
 
 9.
 For
a.
and
b.,
identify
the
electrophile
and
nucleophile
in
each
of
the
following
 reaction
steps.

Then
draw
curved
arrows
to
illustrate
the
bond‐making
and
bond‐ breaking
process.

For
c.
and
d.
also
identify
the
electrophile
and
nucleophile
and
 then
draw
what
the
final
product
(not
the
carbocation
intermediate)
of
the
reaction
 will
be.
 Cl a) elect. b) nuc . + Cl nuc . H I + + I elect. + H Cl c) nuc. Br elect. + H Br Br Cl Br d) Br 
 
 10.
 Draw
the
complete
mechanism
using
curved
arrows
to
show
the
flow
of
electrons
 for
the
acid
catalyzed
reaction
of
(Z)‐3‐methyl‐2‐pentene
with
isopropanol.
 H 3C H 3C C H H 2C C CH3 CH3 H3C OH nuc. elect. Br H 2C C C O CH H3C CH3 CH3 + H C CH3 H2SO4 H H + H CH3 HSO4 H H 3C H H C H 2C C CH3 CH3 H 3C + H C CH3 OH H3C H H C H2C C O CH H 3C CH3 CH3 H CH3 
 11.
 
 For
each
molecule
assign
the
priority
of
the
groups
attached
to
the
central
carbons.

 Number
the
groups
1‐4
starting
with
1
for
the
highest
priority
group.

Also,
assign
 each
asymmetric
carbon
as
R
or
S
configuration
basted
on
your
priority
numberting.
 Br C Cl I F H S C R HO O C H R C R HO O C H O S Br NH2 H S Br 
 
 12.
 Identify
the
asymmetric
center
in
the
molecule
below
and
assign
it
as
R
or
S
 configuration.
 O R 
 
 13.
 How
many
asymmetric
centers
does
cholesterol
have?

Circle
the
asymmetric
 carbons
in
each
molecule.
 H H HO H 
 
 14.
 Chloroamphenicol
has
the
structure
shown
below.
 a)
What
are
the
configurations
(R/S)
of
C1
and
C2?
 b)
What
configurations
(R/S)
would
the
enantiomer
of
ephedrine
have
on
C1
and
 C2?
 c)
What
configurations
(R/S)
would
diastereomers
of
ephedrine
have
on
C1
and
C2?
 HO H C1 C2 HN C O H CH2 H2 C Cl OH cholesterol 
 a)
C1:R
C2:R
 b)
C1:S
C2:S
 c)

C1:R
C2:S
or
C1:S
C2:R
 15.
 Which
of
the
followingmolecules
have
delocalized
electrons?

Draw
resonance
 structures
for
those
molecules
that
have
delocalized
electrons.
 O 2N a) b) O c) H2C C H C H CH2 H2C C H C H CH2 d) O CH2 O CH2 CH2 CH2 CH2 e) f) O C H3C NH2 H3C O C NH2 

 16.
 Which
charged
species
is
the
more
stable?
 
 NH2 OH a) C H 3C NH2 or C H3C NH2 b) O or CH2 O CH3CHCH CH3C CHCH3 
 17.
 Which
resonance
contributor
is
more
stable
in
the
following
resonance
structures?
 O O O C H3C OH H3C O C OH a) c) CH3 CH3 b) d) HC H3C CH C H3C C HC CH2 
 ...
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