Download 1. Name the following molecules using systematic naming. 2. Show

1.
Name
the
following
molecules
using
systematic
naming.
O
O
b)
a)
c)
C
Br
d)
C
Br
OH
OH
Cl
benzoic acid
bromobenzene
1-bromo-4-chlorobenzene
f)
e)
OH
g)
Br
3-bromobenzoic acid
2-methoxypropane
OH
i)
h)
Cl
OH
O
2-methylbutan-1-ol
2-methoxypropane
or
2-ethylcyclohexanol
4-chloro-3-ethylpentan-2-ol
j)
k)
O
O
2-sec-butoxybutane
isopropylmethyl ether
l)
Br
O
O
N
H
Cl
OH
O
OH
ethyl 3-chloro-4-methylpentanoate
O
m)
N-isopropyl-2-methylbutanamide 5-bromo-2-hydroxyhexanoic acid
n)
O
Cl
Br
4-bromopentanoyl chloride
O
O
butanoic anhydride
2.
Show
the
expected
products
of
substitution
reactions
for
the
following
reactants.
Indicate
whether
it
would
undergo
an
SN1
or
SN2
reaction
and
WHY.
H2
C
H 3C
Br
+
OH
H3C
H2
C
OH
Br
+
Br
H3C
H2C
OH
‐This
reaction
undergoes
SN2
because
the
secondary
carbon
that
needs
to
be
attacked
by
the
hydroxide
would
not
make
a
stable
carbocation
intermediate
so
the
halide
needs
to
be
pushed
off
by
the
attack
of
the
nucleophile.
Also,
there
is
little
crowding
around
the
carbon
to
cause
steric
hindrance
against
the
nucleophile’s
attack.
CH3
H 3C
C
CH3
Br
+
H2O
H 3C
CH3
C
+
+
H
+
Br
CH3
CH3
CH3
Br
OH
H 3C
C
CH3
+
H2O
H3C
C
CH3
H
O
H
‐This
reaction
undergoes
SN1
because
the
tertiary
carbon
that
needs
to
be
attacked
by
the
hydroxide
makes
a
stable
carbocation
intermediate,
so
the
halide
can
spontaneously
dissociate
allowing
for
the
nucleophile
to
attack.
Also,
the
3
methyl
groups
surrounding
the
central
carbon
may
sterically
inhibit
the
nucleophile
from
attacking
before
the
halide
dissociates.
3.
Show
the
expected
products
of
elimination
reactions
for
the
following
reactants.
You
need
to
decide
if
it
is
an
E1
or
E2
reaction.
H CH3
H
C
H
C
Br
+
H 2C
OH
CH3
C
CH3
+
Br
CH3
CH3
H 2C
C
CH3
Br
+
H2O
CH3
H 3C
CH3
C
Br
+
H2O
C
+
H 3C
CH3
CH2
H3O
+
Br
CH3
Br
+
H 3C
C
+
H2O
C
H
H
H
4.
Name
the
following
reactant
specifying
the
stereochemistry
as
R
or
S.
Show
the
product
of
an
SN2
reaction
with
a
hydroxide
ion
and
name
it
with
stereochemistry
specified.
H 3C
H3C
CH2
CH2
+
H
H 3C
Br
OH
OH
H3C
H
(S)-2-bromobutane
(R)-butan-2-ol 5.
Name
the
following
reactant
specifying
the
stereochemistry
as
R
or
S.
Show
the
product
of
an
SN1
reaction
with
a
hydroxide
ion
and
name
it
with
stereochemistry
specified.
H3C
H3C
H3C
+
H
H3C
CH2
CH2
CH2
+
H2O
Br
(S)-2-bromobutane
OH
H3C
H
(R)-butan-2-ol
6.
Show
the
major
products
of
the
following
reactions.
H
H3C
OH
(S)-butan-2-ol
OH
H2CrO4
OH
O
H2CrO4
OH
O
H2CrO4
NR
OH
HI
O
O
2
+
H2O
I
Δ
O
H
CH3OH
HO
O
OH
CH3O
CH3OH
O
O
O
+
+
Cl
HCl
O
OH
O
O
+
NH2
2
+
N
H
Cl
NH3
Cl
O
O
+
H2O
HCl
+
OH
Cl
O
O
HCl
+
O
H2O
OH
O
HCl
HO
+
O
O
+
HO
O
O
H2N
+
N
H
O
O
HO
O
O
O
+
2
H2N
HO
O
O
+
+
N
H
+
O H N
3
NaOH
O
H2O
+
O
O
Na
+
HO
O
H
N
HCl
H2O
+
OH
+
Δ
O
Cl H3N
O
H
N
+
Br
HBr
CH3OH
O
H 3N
+
Δ
O
O
7.
Show
the
mechanism
of
base
catalyzed
hydrolysis
of
ethyl
pentanoate
with
sodium
hydroxide
as
the
base.
O
O
NaOH, H2O
Na
O
O
O
+
HO
O
O
+
OH
+
Na
OH
+
Na O
O
O
8.
How
would
you
go
about
adding
a
single
chlorine
substituent
to
benzene?
Show
the
mechanism.
OH
Cl
FeCl3
Cl2
+
HB
+
B
H
Cl
+
Cl
FeCl3
Cl
FeCl4
+
9.
This
is
the
final
step
in
synthesizing
aspirin
(acetylsalicylic
acid).
Given
these
reactants
and
what
you
know
about
anhy
dride
reactivity
show
the
structure
of
aspirin.
O
O
O
O
OH
+
O
H3PO4
OH
OH
O
O
10.
Show
the
major
product(s)
of
the
following
reaction,
if
any,
and
give
a
mechanism.
OH
+
H
Δ
Br
Br
+
H2O
Δ
OH2
+
Br
11.
Show
the
major
product(s)
of
the
following
reaction,
if
any,
and
give
a
mechanism.
Compare
this
reaction
to
that
of
#10,
and
reason
why
they
are
different.
NH2
+
HI
NR
Amines
do
not
undergo
substitution
reactions
like
alcohols
because
an
anionic
amine
( NH2 )
is
too
strong
of
a
base
to
be
a
good
leaving
group.
Hydroxide
( OH )
however,
while
a
strong
base,
can
be
forced
to
leave
with
heat
and
an
acid
present.
12.
Show
the
mechanism
of
the
following
elimination
reaction
and
show
ALL
products.
Rank
the
products
from
most
to
least
prevalent
in
the
product
mixture.
most-->least prevalent
H2SO4
OH
+
+
Δ
+
HSO4
H3O
H
OH2
H2O
H
H
or