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20.

3) Which compound in each pair is more reactive


toward nucleuphilic attack?
O O
O
a)
H3CH2CH2C H3CH2CH2C H
H3CH2CH2C H

O O
O
b)
H3CH2C
H3CH2C
H3C(H3C)HC CH2CH3

O O
O
c)
H3CH2C Cl H3CH2C Cl
OCH3

d) O O O

OCH3 OCH3
NHCH3

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20.4) What alcohol is formed when each
compound is treated with NaBH4 in MeOH?
a) O OH
NaBH4
H3CH2CH2C H
MeOH
H3CH2CH2C H
H

b) O OH
NaBH4
MeOH

c)
NaBH4
MeOH

O OH

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20.5) What aldehyde or ketone is needed to synthesize
each alcohol by metal hydride reduction?
OH O
a)

b) OH
O

c)
OH O

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20.6) Why cant 1-methylcyclohexanol be prepared from
a carbonyl by reduction?

OH

Tertiary alcohols can not be made by reduction of a


carbonyl because there are no hydrogens on the
carbon with the -OH.

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20.9) What reagent is needed to carry out the reaction
below?
O HO H

Cl Cl

Two reagents are needed to carry out this


reaction. First, the (S)-CBS reagent to
produce the R-enantiomer. Followed by H2O
to protonate the alcohol.

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20.11) Draw an acid chloride and an ester that can be
used to produce each product.
a) O O
CH2OH

Cl OCH3

Cl
OCH3
b)
O
OH O

c) OH H3CO

H3CO Cl

H3CO

OCH3

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20.12) Draw the products of LiAlH4 reduction of each
compound.
O
a)
OH OH

O
b)
NH2 NH2

O
c)
N(CH3)2 N(CH3)2

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20.16) Predict the products of the compound below when
OH
reacted with each reagent.
O

HO

a) OH

NaBH4
MeOH OH

HO

b) LiAlH4 OH

H2O
OH

HO

8
OH

HO
c) O
PCC
O

OH O
d) Ag2O
NH4OH OH

HO

O O

CrO3
e)
OH
H2SO4, H2O
HO

O
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20.17) Write out the rea tions needed to
convert CH3CH2Br to each of the following
reagents.
a) H3CH2C Li

H3CH2C Br + 2 Li H3CH2C Li + Li Br

b) H3CH2C MgBr

H3CH2C Br + Mg H3CH2C MgBr

c) H3CH2C CuLi

H3CH2C Br + 2 Li H3CH2C Li + Li Br

2 H3CH2C Li + CuI Li + Li I
Cu
H3CH2C CH2CH3
10
20.19) Draw the product of the following reactions.
a) Li

+ H2O + LiOH

b)
MgBr + H2O + HOMgBr

c)
MgBr + H2O
+ HOMgBr

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20.20) Draw the product formed when each compound
is treated with C6H5MgBr followed by H2O.
a) O H

OH

H H
H

b) O CH2CH3

OH
H3CH2C CH2CH3
CH2CH3

O
c) CH2CH3

H3CH2C H OH

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d) OH

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20.23) What Grignard and carbonyl are needed to
prepare each alcohol?
OH O
a) + H3C MgBr

MgBr
O
OH
b) +

H H

O
OH

c) + H3CH2C MgBr

or
O
MgBr
|+

14
d)
OH
O

+ H3C Br

or

MgBr
+

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20.24) Tertiary alcohols with three different R groups on
the carbon attached to the OH can be prepared in three
different ways using the Grignard reagent. Show them.
a) OH
O
H3C CH2CH3
CH2CH3 + H3C MgBr
CH2CH2CH3
H3CH2CH2C

O
+ H CH C MgBr
3 2
H3C

CH2CH2CH3

+ H CH CH C MgBr
3 2 2

H3C CH2CH3

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b) OH

O
+ H3C MgBr

O MgBr
+

MgBr
O

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c) OH

+ MgBr

MgBr
O
+

+ H3CH2C MgBr
O

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