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Date:_____________________________

Exam III
Practice Exam
Chem. 212

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1 of 12

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HO 3
CH2CHCH3
CHCH3
CHCH
O OO ONaNO2, HCl, H2O,O 0C
OO O
O O
O
CH
CH
H3CH
CHCH
2CCHCOCH
2CCHCOCH
3 3
3CH
3CH
2CCHCOH
2CCHCOH CHCH
3CH
3CH
2CCH
2CCH
2 23
CH3CHO
CH2CH2CH2CNCH
2CH2O
LiAlH34 O O LiAlH4, (CH3CHO
2)2O
CNCH3
O
CHCH
CHCH
CHCH
2CH
2CH
22CH
2CH
32CH
3 2CH3
2CH
2CH
2CH
2CH
3 3
2CH
2CH
2CH
2CH
3 3
CH
CH
NO
CH3CCHCOCH3
CH3CCHCOH
CH3CCH2
NO
CH3CNCH3
Na
Cr
O
,
H
SO
,
H
O
CH2CH2CH2CHO
CH
CH
CH
CH
CH2CH2CH2CH3
2
2
7
2
4
2
3
2
2
2
3
CH3 NO
CH
CH
CH
CH
CH
CNCH
3
2
2
2
2
3
O OO O
O OO O
O O
O
O
CHCH23CH3 3
O O H
O O
O
CHCH
CH
CH
CH
CH
3CCHCOCH
3CCHCOCH
3CCHCOH
3CCHCOH
3CCH
3CCH
2 2
H3NO
O+
KOH, H2O, (CH3CH2)2O, 0C
HO
O
CH
CH3CH2CCHCOH
CH3CH2CCH2
CHCH
CHCH
CHCH
2CH
2CH
2CH
2CH
2CH
2CH
3 3
2CH
2CH
2CH
2CH
2CH
2CH
3 3
2CH
2CH
2CH
2CH
2CH
2CH
33CH
3 2CCHCOCH3
+, H O
Solvent
light
h

Slow
H
Fast
2
O
CH
CH
CH
CH2CH2CH2CH3
CH2CH2CH2CH3
3CH
2MgBr
2CH
2CH
2CH
2CH
3 2CNCH3
Q) Provide
the product of this reaction:
CCH3
CCH2CH3
O OO O
O OO O
O O
NO
LDA
CHBr2
CH2
CH3
+ CH2CH2CH2CH3
H
CHCH
CHCH
3CH
2CCHCOCH
2CCHCOCH
3 3
3CH
3CH
2CCHCOH
2CCHCOH
3CH
3CH
2CCH
2CCH
2 2
O
N
N
Solvent
light
h
HN(CH(CH
)
)

Slow
Lithium
diisopropylamide
Fast
3 2 2
MgCl
PF6!
CHCH
CH
CHCH
CHCH
2CH
2CH
2CH
2CH
2CH
2A)
3 3
2CH
2CH
2CH
2CH
2CH
2CH
3 3
2CH
2CH
2CH
2CH
2CH
2CH
3 3 +
CO
2 2CH2CNCH3
CH
3CH
CH2CH2OH
Br
CBr3
LDA
(CH3 3CHNO
2) 2O
CH2CH2CH2CH
+ether
CH CH3 N Diethyl
N
BMIM hexafluorophosphate
OO
OH
Pyridinium chlorochromate
PCC
Acetone !
HN(CH(CH3)2)2
Lithium diisopropylamide
CH3COCH3
PF
OH
OCH
NH
6
2CH3 O N
2 CH
O
N
CH
CN
COH
CH
CH
CNCH
2
2
2
3 2 2
3
Ammonia
NH3
CHCH3
Br
O
PyH+, CrO3Cl-, CH2Cl2
Acetonitrile
Q) Provide
the
name
for
this
compound:
CH3CN
NO
Water
(CH3CH2)2O
H 2O
Diethyl ether
CHCH3
CH
A) benzenamine
O 3
OHCH2OSBMIM hexafluorophosphate
OH
Ethanol
DMF
CH3CH2OH
HCON(CH3)2
Acetone
CH3COCH3
O
Ammonia
CHCN
CH COH
NH3
CH3OH
+Methanol
N !H
Dimethyl formamide
Acetonitrile
CH3CN
Water
H2O
Isopropanol
(CH
3)2CHOH
CH2CN
CrO3Cl!, CH2Cl2
CH2OCH2CH3EthanolDMSO CH2OH
DMF
CH3CH2(CH
OH3)2SO
HCON(CH3)2
CH25C
Propanol
3
MnO2,chlorochromate
acetone,
CH3CH2CH2OH
Pyridinium
!,
PCC
1) KMnO4, OH
Q) Predict the product of this reaction:
Dimethyl
sulfoxide
Methanol
CH
OH
3O
+
Dimethyl formamide O
Formic acid
2) H , H2O PyH+, CrO Cl-, CH Cl
O2, acetone, 25C
HCOOH
3
2 2
HMPA
Isopropanol
(CH
((CH
3)2CHOH
COH
3)2N)3PO
O
CH 3)2SO
Acetic
DMSO
3COOH
NaBH
NaBH
(CH
4 acid
3CH
2OH
O 4, CH
O CH
HOCH CH
NaOCH
2CHCH
3, CH
3CH2OH
Propanol
3 triamide
2
2OH
COH
A)
Hexamethylphosphoric
Formamide
HCONH
O
O
O
O 2CH2CH2CH2CCHCOCH2CH32
CH3CH
Dimethyl sulfoxide
O
Formic acid
+ N !H HCOOH
N-methylformamide
HCONHCH
COH
CH
CH
CH
CH
CH
CH
COH
O
3
2
2
2
2
2
CH
CH
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CH
CH
CBr
3
2
2
2
2
2
3
2
2
2
2
2
LiAlH
CH3NO2
LiAlH4,
O 33
Nitromethane
CH(CH
4
3CH
2)22CH
2CH
2CH
HMPA
((CH3)2N)3PO
CH
3CH
2CH
2CH2CH2COCH2CH3
!, CH
O
CH
O
O
Acetic
acid
CrO
Cl
Cl
3COOH
3
2
2
O
COH
(CH3)3COH
tert-butyl alcohol
CH3Formamide
O CH
N,N-dimethylformamide
HCON(CH
3)22CH2CH2CH2CBr
O 32CH
Hexamethylphosphoric
CH
CHthis
COH
3CH
2CH2of
23CH2reaction:
CH
3CH2CH2CH2CHHCONH
2CCl + CH
Q)3CH
Predict
the
product

2
CH
CH
2CH2triamide
2CH
2CH
2CNHCH
3NH
Na2Cr
O
O CH CH CH COCH CH
O 2O7, H2SO4, H2O CH3CH2CH2CH2
COH
O
CH
3
2
2
2
3
N-methylformamide
HCONHCH
32
CH3NO2
Nitromethane
O
O
CH3CH2CH2CH2COH
CH3CH
CH
2CH2CH
2CCl NaBH , CHOCH
3CH2CH2CH2CBr O
O
NaBH
2CH2CH2CH2CNHCH3
4 O
4
3
2OH
A) CH3CHNaOCH
(CHO
3)3COH
HO
2CH
3, CH3CH2OH O tert-butyl alcohol O
+O
O
H
H
O
3
O
N,N-dimethylformamide
HCON(CH3)2
CH3CH2CH2CCHCOCH3
CH3CH22CH
CH32COCH3
HO
CH3CH2CH2COH
CH
2CH2CCHCOCH
O2CH2COH
CH3CH
CH3CH2CH2CCl
CH3CH2CH+2CBr CH CH
O
CH3CH2CH2CH2CNHCH
3
2
3
LiAlH4
H ,O
H2O
LiAlH
4,2(CH
CH
O33CH2)2O
2CH
O 2CH
Q) Provide
key2CH
product
ofO2this
CH3the
CH2CH
CH3 reaction CH3CH2CNCH
2CH2COCH
O
CH3CH2COCH3
CH3CH2
CH3CH2COH
CH3CH2CCl
A) CH3CH
NH2CNHCH
O O CH3CH2CBr
2CH
2
CH
O3
3CH2
2CH
O
O
O
O
O
O
Na2Cr2O7, H
4, H2O
O
O2SO
O
CH3CH2CH
2CCHCOCH2CH3
CH3CH2CHO
2CH2COCH
2CH3
CH
O 3COH
CH3CCl
CHCH
CH2CH
3CCH2COCH3
3CBr
3COCH3
O
HOC
COH
CH3CH2CNHCHO
O
3
O +O
O
CH
2CH2CH3
H
H3O
O
O
O
HO O
CH3COCH
CH
CH
3CH
2CH
2CH
2CH3
CH33CH=CHCH
CH
Q) Provide theH2name
2CH
2CCHCOCH
3 2COCHCH
CH3CHfor
COCH
CH3CO
2CH
2this
3 3 CH
2CH
3 H22C=CHCH
C=CHCH
2CH
2CHcompound:
2CH
2
2CH2CH2CH2CH3
CH3CCH2COCH2CH3
CH3COCH2CH3
CH3CNHCHO
3
+, H O
O
Br
Br
H
Br
2
CH2CH3
O O
A) ethyl hexanoate
CH3CH=CHCH2CH2CHO
3
O O
O2COCH
O 3
CH
3CH2CH2CH2CH2COCH3
CH3CH
O O
CH3CHCHCH2CH3 BrCH2CHCH2CH
CH2CH
O
3CH
2CCHCOCH
2CH
2CH2CH3 3
O
CH3CH2CH
CH=CHCH
2CH3
CH3CCHCCH
3
3CCHCCH3
O 2CH2CH2CH2CH
CH3CCCH
3
2CH2CCHCCH2CH2CH3
NaNH
NH
HCCCH
2
3
2CH
3
O2CHO
O
CH
CH
CO
CH
3
2
3
CH3CH2COC
2
CH3H2C=CHCH2CH
CH2CH=CH
NaOCH
2CH3
3, 2CH
33OH
HCCCH
CCH
CH3I
2CH
2CH
CH3CH2I
CH
3CH
23CH2COCH
CH2CH3
CH33CCHCH
2COCH
Q) Provide the
product
of3COCH
this
Br CH
Br reaction:
3
O
O O
O O
CH3CH2CH2CH2I O
2CH3 CH3CH2CH2I
O
BrCH2CHCH2CH2CHCH2Br CH3CHCH=CHCH
CH3CH2CH2COCH3
CH3CCHCOCH3CH3 CH3CCHCOCH3
H3C Br Br
CH3CH2CH2CH2COCH2CH3 CH3CH2CH2CH2COC
O
O
CH3
CH2CH3
A)
CH3CHCHCHCH
2CH3
O
O
O
CH3CHCHCHCH2CH3
O
CH2CH
CH2CCH3
CH3
O O
O O
O
O
!
COCH
CH
2
3
HCCH
HCC O
2CH
CH3COCH
CH
3 2CH2CH2CH2COCH2CH3
O
O 3 CH3CH
CH3CCHCOCH2CH3 !CCH
CH3CCHCOCH2CH
3 !
!CC
CH2CH
CH2CCH3
O
O
3 3CC!
CH3CCHCHCH
CH3
CH2CH3
CH3
CH2CH2COCH2CH3
CH3CH
CH32CH2CH2CH2CH2COCH3
O
O
O
O
CH3CH2Cu
CH3CH22CH
OK,
CH3 2CH2OH, (CH3CH2)2O
O O
!CCCH
CH
2
!CCCH
O
CH
=CHCH
CH
CH
CH
CH
3
2
3
2
2
CH
CH
CHCH
Q) Provide the product
of this reaction:
+CH2CCH
3
2
!
!CCH
!CC
CH
2CH
3
COCH
CH
COCH
COCH
CH
2
3
3
2
2
3
CH
CH
OCCHCOCH
CH
2O 3
O 3 2
O
CH3CuLi
CH3CH2OK, CHO
)2O2
2CH2OH, (CH3CH32CH
CH
OO
O CH3
3
O
CH32CH
CH2CH2CH
O
CH2CH2CCH3
CH2CH2CCH2CH
CH3CH
2CH2CH
2CH
!CCCH
2CH3
!CCCH
2CH3
CH3
CH3
O O
CH
CH
CH
CHCH
3
2
2
CH3
!CCH
!CC!
O
CH3CH2OCCHCOCH2CH3
CH3
O
CH3CH2CH2CH2CH2CH
A)
CH3C
CH2CH3
CO
!CCCH3
CCH
O 2CH3
!CCCH2CH2CH3
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
O
O
H2CCH3
!CCH
!CC!
CH
CH
CH
CH
CH
CHCH
CH3CH2CH2CH2CH2CH2CH
3
2
2
2
2

!
=

=O

=
!
=

=
=

=
=
=

=
=

=
!
=

= =

2 of 12

=O

=O

=O

! =
=

=O

=O

=O=

== =

=
=
!
=

=
= != == =
=
=

! =
=

! =
=

! =
=
=

=
=

=
= =

=
=

=
=
=
= = =
=

! =
=

! =
=

=
!
=

! =
=

=
=! =
=

= =
=

=O

OH

=
=

= =

OH

CH3

CH2CH2CH2CH3

Br

+LiAlH4, (CH
CH ) O !
3
2 2
CH
3

!
CCH2CH3

CCH3

H3O+

=O

Cl

SO3H

=O

=O

CHCH2CH3
Na2Cr2O7, H2SO4, H2O

MgBr

=O

LiAlH4

3
CH NO22CH2CH2CN
CHCH
Q) Provide the key product of this reaction: (CH3)2CHCH
+ [(CH
3)2CHCH2]2AlH

Toluene

H+, H2O

MgCl
O
SO3Na
CH2CH3
CH3CH2CH2CH2CH2CH2CH
OH
O
OH
OCH2CH3 1) KMnO4, OH!NH
, 2
CH3CH2CH
SO2Cl
CH2CH
2CH
2CH
CHCH3
2CH
2CH
3
+
!
++
!
O2) H , H2O
Predict the product of this reaction:
O
CH3CH2CH2CH2CH
NHCCH3
O2N
CH2CN
O2N
CH2COH
O
COH

=O

=O

Q)

2OH
+
CH22CH
! 2CHO
A) (CH
CH
3)2CHCH
2CH

CH3CH2CH2CH
O

OH O

!
=

OH
CHCN

A)

CH COH

CH3CH2CH

Pyridinium chlorochrom
PCC
Q)Which one would be expected to have the highest boilingOpoint?
NaOCH
2CH3, CH3CH2OH
OH
A. CH3OCH3
-, CH
2CH
CH3CH
PyH+, CrOCH
3Cl3CH
2Cl22CH2CH2
O
B. CH3CH2OH
CH3CH2CH2CH2CH2COCH2CH3
C. CH3CH2NH2
O
O
H
=O

=
=
!

=
=
!

=
=
!

3 of 12

= ! == =
=

O
O
CH CH OK, CH2CH2OH, (CH3CH2)2O
+ CH2=CHCCH3 3 2
CH2CH2CCH3
COCH2CH3
CH3
O

= = =

=
=

=
=

Q)

CH2=CHCCH3
O CH3
O CH3CH2OK, CH2CH
O 2OH, (CH3CH2)2O
O
O
O
O
CH
CH
CCH
CH
OCH
CH
OCH
2
2
3
3
2
2
3
Provide the product
of this reaction:
CH2CH
CH2CCH3
CH3
CH3 O
O
CH3
CH3
O
COCH2CH3

SO3Na

=
= =
!

= ==

=
=
!

=O

A)

=O

=
=

=
=

=
=
= = =

=
=

Br

O
+ N !H
HO
Br
H
H
Br
HCH
CH
3CH CH3CH2CH2CH2COCH2CH3
O
O
O
HCOCH
2CH2CH2CCH3
3
H
H
CH
3
D.
CrO3Cl!, CH2Cl2
O O
O
O
O
O O
O CH3
O
O
CH
CH
CH
CH
CH
CH
COH
3
2 3 2
2
2
CH
CH3CH2CH2CH2CH2CH2CBr
CH
3 3CH2CH2CH2CH2CH2CCl
H CH3
Br2 CH
CH
Br
3
O
3CH2CH2CCHCOCH
CHO
CH CH COCH3 CHCH
O
OHCCH2CH2CH32CCH
CH3 3HCCH2CH
23CH22CH22CH3
3CCH2CH2CH2CH3 CH
O
O
HCH
E. CH
CH32CH
Br
H
H
3
O
CH3CH2CH2CH
CH
CCH(CH
)
O
2CH3
2CH
2
3
2
CH
CH
CH
CH
CH
COH
2CH3
3
2
2
2
2
CH3CH2CH2CH2CH2CCl
CH3CH2CH
2CBr
O 2CH2CHO
O
O
O CH
O
3COCH3
CH2CH2CCH
O3
OH(B)
A)CH
Cl
NaBH
O
4
4, CH3CH
O
OCHO3CH2COCHNaBH
H HO
NaOCHH2CH3, CH3CH2OHO
3
Cl
H
Cl
HCCH
CH
2
3
=O
CH3CH
2CH
2CH
2CH
2CCHCOCH
3
CH
CCH
HCCH
HC
H
CH
2CH
2CH
2CH2CH 2CH
2CH2CH2CH2CH
3 2CH
CH2CCH(CH
3CCH
H2CH3
CHCH
)2 2COH
3CH2CH23CH
CH3CH
CH
3CH
2CH32CHH
2CH
O
O 2CCl
2CH
33CH2CH
2CH
2CBr
O
H
O OO O
O CH3 O
O3
O CHCH
CH
CH
CH
CH
CH
2
2
2
3
O
O
3
(CH3C3
CH2CH2COCH2CH3 O CH3CCH2CH3
Cl
CH3
4
3CH2CH2Cl
CHLiAlH4,
CH3COCHLiAlH
3CCH2COCH
3
HC=O
H 3
CH=CH
2 ) CH]
CH23CH2CCH
CH
)
HCCH
H
22CH
CH
CH
COH
2CH
2CH
2CCH(CH
3CH
2 of
2CH
HCCH
CH
3
2
2
CH
CH
CH
CCl
CH
CH
CH
CBr
2
3
3
2
2
3
2
2
Q)3CH
Predict
the
product
this
reaction:
+
[(CH
CuLi

3
2
2
O
CH3
Cl
H
O O CH O
O O
O
O
O
O
O
3
H
CH
CH
O
3
2
H
CH
CH2Cr
2O7, H2SO42, CH
2O
3CH2CH2Na
2CCHCOCH
3
HCCH2CH2CHCH
C=C
CH3CH2CHCH
CH
3
2Br
2COCH2CH3
O Br
CH
CH3HCCH
CH3CH2COH
3 CH3COCH2CH
2COCH
3
Br
3CH2CCl
3CH2CBr
CH
2CH
CH
CHA)
CH23CH23CHBr
3
3CCH
2CH
3 3
2CCH(CH3)2
O O O OO
CH3CH2
CH
H
2CH3
O
O O
O
CH2CH
2CH3
O
O
O O E
O
O
CH3CCH
3CH22CH
3 H
CH3CH2CHCH
CH3COH
CH
CH22CCHCOCH
CH3 CH3CBr
2COCH
H
3CCl 3
H 3O +
OH
OCH
3
2CH3
3)2
OH
OCH3 HO
HCCH
CH23CCH
CH
CCH
2CH
2CH
3CH2CCH(CH
3
O
O
CH
CH=CH
3CH2CH2CCHCCH2CH2CH3
23
CH2CH3
O O
O
O
NaOCH
H+, H2O
O 3, CH3OH
O CH
CH3CHO
2COCH3 + CH3CH2CCH2CH3
2CH3
Q)
Provide
the
product
of
this
reaction:
CH
CH
CCHCOCH3
O
3
2
CH
CH
CCH(CH
)
2
3
3
O
FO 3 2
CH3CCH2O
CH2CH3
CH2CH
CH2CH2CH
O 3 O
OCH3
CH
O
O
O
O
CH3
O
C
Cl
Cl
Cl23OCH3
CH
CH3CH2CCHCCH
CHCl
2CH3
3
CH
CH
COCH
3CCH2COCH3
3
3
CH3CH2CCH2CH3
CH3COOH
CH3 Br
A)
CH2OCH3
O
CHCl3
O
OH
OCH3
OH
OCH3
CH2OCH3
Pt
H
,
Pt
2
CH2Cl2
O
CH3COOH
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
O
PtO
2
CHClH3 2, PtO2
CH2CH2CCH
CHCl3
CH2OCH2CHO
O
Cl 3
3
OCH3
SO3H
CH
OCH
2
3
O
O
O
O
Pd, C
H2, Pd, C
CH3the product
CHQ)
2Cl2Provide
of
this
reaction:
CH
CH
CH
CH
CH
2
2
2
CH3
CHCl3
RaneyCH
Ni3 H2, Raney Ni
CH3
CH2OCH3
CH3
NO2
O
O

CH3CH2CH2CH2CH2CNCH3
NO
O

! =

KOH, H2O, (CH3CH2)2O, 0C

CH2=CHCCH3

CH3CH2CH2CH2CNCH3

CH3

OH
O

CH
2CN
CBr
3

OH O
Br COCH2CH3
O
CH COH
CHCH
CH2OS
O3

=O

CCl2CH3

= =

A)

CH2COH

CH

!
=

CHCN

O2N

!
=

OH

Br

COCH2CH3
O2N

CH3

O
CF3

CCl3

CH2CN

! =

NO
O
Pyridinium chlorochromate
PCC
CH3CH
2CH2CNCH3
PyH+, CrO3Cl-, CH2Cl2
NO
O

CH2

! =

CHBr2

CH
+ N3CH
!H2CNCH3
NO
CrO3Cl!, CH2Cl2

CH3

NaBH4
CH2OH

CH2OCH2CH3
HO

PCC

OH

=O

Pyridinium chlorochromate

PyH+, CrO3Cl-, CH2Cl2

NaBH4, CH3CH2OH+ N !H

= =
=

=
=

=
=

=
=
!

4 of 12

3 3 3

=
!
=

=
=

=
=

=
=

===

=
=

=
=
= =

=
=

=O

=
=

OH

=
=

=O

!
=

=O

OH

=O

=O

=O

=O

=O

=
=
= =
=

=O

=O

Q)3 Predict
product(s)
of thisCHF
reaction:
+ HCl
CrO3Cl!, CH2Cl2
CBr2CH
2
O theCHCl
O 2
H
CH
3
O
O
LiAlH4 O
LiAlH4,
(CH3CH2)2O
HCH CH3CH
CH3
CH3
CH
3
CH3 3CH2CH2CH2CH2CH2COH CH3CH2CH2CH2CH2CH2CCl
CH3CHO2CH2CH2CH2CH2CBr
CH
O
O 2CH
OO CH2Cl
O
CF2CH3 O
CH
CHCH
CHCH3 Na2Cr2OO7, HCHCH
3 2O
2F 3
2SO4, H
NaBH4
NaBH4, CH3CH2OH
CH
3COCH3HO
CH2Br
CH2CHCH
COCH
CH
2CH
2
2
3
CH
CO
32CH2CH2CCl
CH
CH
COH
3CH2CH
2
2
2
CH
CH
CH
CH
CH
CH
CH
CH
CBr
CH
CCH
3
2
3
2
2
2
2
3
3
A)
+
H
O
2O
O
CH
3
O H
O
O
OO
+
H
H
O
3
LiAlH4
H
LiAlH4, (CH3CH2)2O
CH
CH
CH
COH
CH2CH2CH2CHCH
COCH
23 2
2
CHHO
CH3CH2CH2CH2CBr
2 3
3CH
2CH
2CH
2CCl
2CH
2CH
2CH3
O CH
HCCH
2CH3
O
O
CH3
O
O
O
O
O 3CH2COCH3 H+, H2O
CH3CH2CO
CH
Q)3CH
Provide
the product(s)
ofCH
this
reaction:
3 2CH
CH
CH
COH
2
2
CH
CH
CCl
CH3CH2CH2CBr
O
3
2
Na2Cr2O7, H2SO4, H2O
ClCH3CH2CH2COCH2CH3CH3CCH2CH3
O
O
O
O
O
CHCH2CH3
O
O
O
3CH2COH + CH3OH O CH3CH2CCl
CH3CH2CBr
A)HCH
OH!, H2O
CH3CH2CH2COCH
3
CrO
CH
OH
O 2CH2CH3
2
H 3O +
O
O 3, H2SO4, HH2O
HCCH
HO
Br
CH
3CH2CH2CH2COCH2CH3 CH3CH2CH2CH2COCH3
O 3COH
CH
CH3CCl
CHCH
3CBr
MgBr2Cl2
CH
(CH3CH2)2O
H2CH3
3
2MgBr,O
H+, HPCC,CH
CCH3
CCH
2O
O
Q) Provide
the
key
product
of
this
reaction
:
CH
CH
CN
3
2
CH
3CCH2CH2CH3
H3
OCOCH3 CH3CH2CH2CH2CH2CH2COCH2CH3
COCH2CH3OCH3
O
O
A) CH3CH2CCH2CH3
Pyridinium chlorochromate
PCC MgCl
CH2CH2OH
O
CH
NaOCH
!Li 2CH3, CH3CH2OH
CH3CH2CH2CH2CH2CH2COCH3
O
+
CH
CH
CH
CH
CH
CC
3
2
2
2
2
PyH , CrO3Cl , CH2Cl2
(CH3CH2)2O O
Cl
H
OH
CH3COOH
C
COCH2CH3
COCH3 OH
COCH2CH2CH3
CH3CH2CH2CH2CH2COCH2CH3
O
CHCH
CHCl
3
3
H3
O
OCH
Q)3 Provide a name
for this compound:
O
+ N !H
O2N
O2N
CH2COH
CH2Cl2 CH2CN
COH
A) phenol
CH3CH2CH2CH2COCH2CH3
CHCl3
CrO3Cl!, CH2Cl2
O O
O
Pyridinium
chlorochromate
CH3 PCC
H
OH
OH O
CH3CH2CH2CCHCOCH3
3CH2CH2COCH3
Q) Which
one best describes
geometry around a nitrogen atom in anCH
amine
CO
CHCN
CHthe
COH
PyH+, O
CrO3Cl-, CH2Cl2
CH2CH3
A. linear
O
O
NaBH4, CH3CH2O
4
NaOCH2CH3, CH
CH3CH2COCHNaBH
3
HO3CH2OH
B. tetrahedral
CH3CH2CH2CH2CH2CCHCOCH2CH3
O
O
O
O O
+ NO!H
CH2CH2CH
C. trigonal planar
2CH3
(CH3CH
)
CH3CH2CH2CH2CH2COCH2CH3
4
CHLiAlH4,
CH3COCHLiAlH
3CCH2COCH
3 2 2
3
H2CH2CH2CCHCOCH2CH3
CrO3Cl!, CH2Cl2
D. trigonal bipyramidal
O
O
OO O
O
CH2CH2CH2CH3
CH3
E. octahedral
Na
Cr
O
,
H
SO
,
H
O
2 3CH
4 2CH
2 2CH2CCHCO
CH3CH2CH2CH2COCH2CH
O
CH
O
O3
CH3COCH22CH2 3 7 CH
3CCH2COCH2C
O O
A)
(B)
O O
O
O
O
CH2C
CH3CH2CH2CH2CH2CH2COH CH3CH2CH2CH2CH2CH2CCl
CH3CH2CH2CH2CH2CH2CBr
NaBH
NaBH
CH3CH2CH2CH2CCHCOCH
4
4, CH3CH2OH
+
CH
CH
CH
CCHCOCH
3
2
2
3
CH
CH
CH
COCH
O 2CH3
3
2
2
3
O
O
HO
H
H 3O
HO
O O
O
2CH
2CH3
CH2CH3
O O
CH3CH2CH2CHCH
2CH
2COH
CH3CH2CH2CH2CH2CCl
CH3CH2CH2CH2CH2CBr
H+, H2O
3OH
O
O
O O 3, CH
CCHCOCH3
LiAlH4
Q) Provide the product
of this Claisen Condensation:
2 CH3CH2COCH3 NaOCH
LiAlH4, (CH3CH
O 2CCHCO
CH23)2CH
CH3CH2CH
CH3CH2CH2CH2CCl
CH3CH2O
CH2CH2CBr
CH2CH3
O 2CH
O 2COH
O
O
CH3
O
O
O
CH3CH2CCHCOCH3
CH23Cr
CCH
CH3COCH3
Na
H2SO4,3H2O
2O72,COCH
2CH2COH
CH3CH2CH2CCl
CH CH CH CBr
O
O 3 2 2O
A) CH3CHCH
3 O
O
O
CH2COCH3
H 2CBr
H 3O +
CH3CH2COH
CH3CH2CClHO
CH3CH
O
O
O
H+, H2O
CHproduct
3COH
CH1)
Q) Predict the
of this reaction CH3CCl + LiAl[OC(CH )O] H
3CBr 2)

CH3CH2CH2CH2CH
O
CH3CH2CH2CH
O

NO2

CH3

CH2CH3

E
O
H
CH3CH2CH
NO2
CH=CH2
CH3
H
Br
H
O
H
Br
HCH CH3CH
NaNOH2, HCl, H2O, 0C
H
CH3
OF
A) CH3CH
O
O
CH
CH
3
3
Br
NO
CH
CH
CH
CH
CH
CH
CNCH3
HCC
2
3
2
2
Br
CH
Br
CH32 2 2
Cl
NO2
NH2
CNCH
3 CCH
O 3
CH
3 bromide,
3
N-dodecylthiazolium
NaOH,
H
2O
O
OH
NO
CH3
Br
H
H NO O
CH3CNCH3
CH3
Br
CH3C!CHCH
O
3
H
Cl
H
bromide,
NaOH, H2O
H
+

H CH2Q)
Cl
Provide
the
product
of this! reaction:
2 HCCH2CH3 N-dodecylthiazolium
NO
CH
Cl
OCH3
OH
3
OCH
3
CH
CH
CH
CH
CH
CNCH
H
CH
3
2
2
2
2
3
3
Cl H Cl
Cl
Cl
O
Cl O Cl
Cl
Cl
OH
OH
CH3
NO
Cl O CHClCCH
Cl CH
Cl
Cl CH3
3 2C!CHCH
H2O, (CH23CH
CH22Cl
)2O, 0C
CH
3KOH,
A) CHCH
3
2
3
Cl
SO
H
3
CH
Cl
NO2
NO2
O
3
Cl H Cl
Cl
O
CH3
Cl Cl2CH3 O OH
Cl2OCH
CH
CH3
3CH2CH2CH2CNCH3
Cl CH
Cl !H HCCH
Cl2CH3 CHCl
CH3CH2CH2C!CHCH+2CH2CH2
2
Br
Cl Br Cl
Cl Br Cl
Cl O
Cl
CH3 CHNO
Cl
OCH3
SO
3
CHBr2
O OH
NO2
Cl
Cl
Solvent Cl Fast
light
O
h
Cl

Slow
OH
CHof
3CCH
2CH
2CH3
Cl
theCltri-substituted
this
reaction:
+ Br2
D
D CHQ)
OH
OCH2CH
CHProvide
3 2CH2CH2 product(s)
3OH
2CH2CH2C!CHCH
OCH3
O
CH3CH2CH2CNCH3
Cl Cl
Cl
Cl
LDA
+

NO
CH3
+ CH2CH2CH2CH3
CH3SO
CH32Na
CCH2CH3
CBr3 !
N
N
Cl
Cl
H3C
Cl
Cl !O2N
D
HN(CH(CH3)2CH
)O
Lithium
diisopropylamide
2 3
PF6
A)
+ 3HBr
CH2OCH3
O
Cl
Cl H3C
Cl Cl OH
CH3CH2CNCH3
Cl Cl
Cl
CH3COOH
(CH3CH2)2O
SO2Cl Diethyl ether
Cl
NO
Cl
D
D
!
Cl
Cl
Q)
Rank
the
acidity
of
these
compounds
(most
acidic
first)
++
CHCl
3
HOOC
COOHBMIMHhexafluorophosphate
COOH
!
3C
OH
OCH3
Acetone
OH
OCH
3
CH
COCH
3
3
O2
NO
NO
2
NO2
2
Ammonia
CH2Cl2
NH3 H C
3
Acetonitrile
CH3CN
CHCl3
Water
H 2O
OH
N
O
OH
O
O
Ethanol
DMF
OH
CH3CH2OH
O2N
CH3 O
HCON(CH
OH
O2N
OH
2N
3)2
CH3COCH3
N
NO2
CH3CH2CH2CH2CH2COCH2CH3
CH3CO
Methanol
CH3OH
O
Dimethyl formamide
CH3 HO
CH3
N
NO2
CH3
Isopropanol
O
(CH3)2CHOH
CH3CH2CH
COCH
ONO
NO2 O
NO2
2CH
3b.
2 2CH2NO
2
O
a.
c.
O2N
DMSO
(CH3)2SO
O
NO2
CH3COCH3 Propanol
O2
CH
CH
CH
CH
CH
COCH
CH
CH
CH
CH
OH
3
2
2
2
2
2
3
O
3
2
2
CH
CO
3
A. b > a > c
CH3CH2CO
CH3CH2COCH3
O2N
NCH3
O 3CH2CH2COCH2CH3 Dimethyl sulfoxide
Formic acid
CH
HCOOH
B. c > a > b
HMPA
O
((CH
CH3CH2CH2CH2CH2COCH3
3)2N)3PO
CH
O
Acetic
acid
3COOH
O
C. a > c > b
O
O
CH
3
O 3CH2CH2COCHHexamethylphosphoric
NO2
Formamide
CHCH
HCONH2
3CH2CO triamide
CH
CH32CH
COCH
D. b > c > a
3CH2CH2CH2COCH2CH
3 3CH
2CH23CH2COCH3
CH3CH2CH2COCH2CH3
N-methylformamide
HCONHCH
3
CH3NO2
Nitromethane
O
E. c > b > a
O
O
O tert-butyl alcohol
(CH3)3COH
CH3CH2CH2COCH
a>b>c
COCH32CH3
2CH2CH2PCC
2CH3
COCH3 CH3CH2CH
N,N-dimethylformamide
HCON(CH
)2 2COCH
3CH
Pyridinium
chlorochromate
CH3CH2CH2CH2COCH2CH3 CH3CH2CH2CH
O2COCH3

! =

=
!

=O

=O

CHCH3

! =

=O

! =
! =

CH

5 of 12

! =
! =

NO
O

CH3CH2CNCH3

= =

Br

CH3CH2CH2CNCH3

Br

CBr3

Q)

=O
=

! =

! =

=O

=O

=O

Q)
A)

=O

=O

=O

=O

CH3CH2CH2CH2CH2CH2COCH2CH3
COCH2CH3 O
COCH3
+ N !H
CH
CH
CH
CH
CH
CH
COCH
3
2
2
2
2
3
Provide the product(s) of this reaction:
+2 CH3CH
2CH2OH
CrO3Cl!, CH2Cl2
NaNO2, HCl, H2O, 0C
CH3
COCH2CH3
COCH3
COCH2CH2CH3
CH3CH2CH2CH2CH
CNCH3
O
+ CHNaNO
3CH22OH
, HCl, H2O, 0C
O
CO
NO
CH3CNCH
3
NaBH4
NaBH
4, CH3CH2OH
HO
CH3CH2CH2CH2CH2CH2CNCH3
NO
CNCH3
O
O
CH
NO3CH2CH2CH
NOLiAlH4
CH3CNCH3
H2NCNCH3
LiAlH4, (CH3CH2)2OO
CO
KOH, H2O, (CH3CH2)2O, 0C
Provide the product(s) of this reaction:
NO
NO
CH3CH2CH2CH2CH2CNCH3
CH2O
2Li
CH3N2 + NH3 + K2CO3 + H2O
CH3CH2CH
Na2Cr
7, H2SO4, H2O
NO
KOH, H2O, (CH3CH2)O
2O, 0C
O
O
O
+
H
H
O
3
CH3CH2CH2CH2CNCH3
HO
O2N
CH2CN
O2N
CH2COH
CH3CH
NO
H+, H2O
O
CHBr
CH
2
2
Provide the key product of this reaction:
O
COCH3

COCH2CH2CH3

A)

+, CrO Cl-, CH Cl
PyHCOCH
3
2 2
O 2CH2CH
CH3CH2CH2CH
2
3

=O

=O

COCH2CH3

OH

A) (A)

Q)

=
=

=O

=
=O

! =

! =

=
!

! =

! =

=
!

=
!

=O

! =

CH2OS
O

CH3

NO
CH2I

CH

==
==

==
=
=

! =
=
=

=
=

=
=
!

! =
==

= ==
!=
=

=
=

=
= != =
=

! =
=

== =

=O

=
!
==

!
=

=
=

=
=

== =

==
=
=
=
=

=
=

=
=
=O

= ==
= =
=
=O
=O

=O

=
=
= =

=
=
!

=O

=O

B. (CH3)2NH
C. CH3NH2
D. NH4+
E. (CH3)3N
A) (A)

Hexamethylphosphoric triamide

N,N-dimethylformamide

Cl O2N
O2N

! =

NO
O

CH3CH2CNCH3
NO

I
Br O2N
NO2
O

NO
2
Slow

+ NH3

NO2h

light

CH3CH2CH2CH2CNCH3
NHCH3
2N
Q) OProvide
theNO
keyOproduct
2N
O

A)

(CH3)3COH

LDA
CH3CH2CH2OH
CH2CH
+ CH2CH2CH2CH3
O22CH
N 2CNHCH3
OCH3 CH3 N
N
NH2 O2N
OH
O
OCH
2N
3
O
HN(CH(CH3)2)2
Lithium diisopropylamide
PF6!
CH3CH2CH2CH2CH2CNHCH3
NO2
O3CH2)2O NO2
(CH
ether
NODiethyl
NO2
NO2
2
BMIM hexafluorophosphate
CH3CH2CH2CH2CNHCH3
Acetone
CH3COCH3
O
Ammonia
NH3
Acetonitrile CH CH
NaNO
H32O, 0C
2, HCl,
CH
CN
O
N
OCH
CH
3
2
2
CH
CNHCH
Water
3
2
2
3
H 2O
this reaction:
NHCH3
O2N
OCH2CH3
O
Ethanol
DMF
CH3CH2OH
HCON(CH3)2
CH3CH2CNHCH3
Methanol
NO2
CH3OH
Dimethyl formamide O
NO2
NO2
Isopropanol
(CH3)2CHOH
CH3CNHCH
3
DMSO
(CH3)2SO
Propanol
CH3CH2CH2OH
Dimethyl sulfoxide
Formic acid
HCOOH
HMPA
6 of ((CH
12 3)2N)3PO
CH COOH
Acetic acid

! =

O2N

NONO2
O

CH3CH2CH2CNCH
3 2
NO

Fast

tert-butyl alcohol

HCON(CH3)2

of

NO
NH2
O
O2N
CH3CH2CH2CH2CH2CNCH3
O2N

NO2
Solvent

NO2
of this reaction:

HCONH2
HCONHCH3

! =

O
NO2
Q)Provide
the
product
CH3CH2CH
2CH2CH2CH
2CNCH
3

Br O2N
Cl O2N

Formamide
N-methylformamide

O2N

A)

CH3NO2

Nitromethane

! =

CH3

CH2CH2CH3 O
3
NaOCH2 CH33,CH
CH2COCH
3CH2OH

OH

! =

H3

CH3CH2CH2CH
2CH3
CH2COCH
O2 O
2CH3
CrO3Cl!, CH2Cl
O O
O
O
O
CH
CH3CH2CH2CCHCOCH3
3
CH3CH2CH2COCH3
CH
CH
CCHCOC
3
2
O
O
CH3CH2CH22CH
CCHCOCH
CHCH
3CH
2CH
2COCH
3CH
2CH
2CH23CH2CCHCOCH
3
O
CH
CH
O
O
O2COH
O
O CH2COH CH
O2N2 3 O2N
CH2CN
O2CN
N
CH
OO
2N
O
CH3 2CH3
CH
CH
CH
CH
CH3CH2COCH3
2
2
2
CH3CH2CCHCOCH
CH3CH2CH32CH
CH32COCH
CH2COCH
3
2CH3 CH3CCH2COCH3NaBH4
NaBH4, CH3CH
CH3CH2COCH3
HO
O
O
O
OH
OH O
O
OH
OHO
O
O
O
O
O
O
O
CH3CCH2COCH3
CH3COCH3
CHCN
CH
COH
CH3CH
CHCN
CH2COCH
COH
2CH2CH
2CCH
2CH3 4
2CH32CH3 CH3CCH2COCHLiAlH
CH
CH
O
3CH
2CH32COCH
(CH
3CH
CHLiAlH4,
CH3COCH3
3CCH2COCH
3
O
O
O
O
O
O
CH
CH2CN
O O
O 2N
CH2COH
O
O
O
CH2CH2CCHCOCH3
CH3CCH2COCH2CH3
CH3CH2CH2COCH3 OCH3O
CHA)
3COCH2CH3
CCHCOCH
2CH3
Na
2Cr2O7, H2SO
4, H2O
PyridiniumCOCH
chlorochromate
PCC
2CH3
CH
CCH
CH2CH
3
2COCH
3COCH
2CH3
CCH2COCH
3
O
CH
CH
2
3
O O
CH2CH2CHO
O
3
O
O
O
PyH+, CrO3Cl-, CH2Cl2 CH3CH2COCH3
CH
CCHCOCH
CH
3CH2CCH
2
3
O
+
COCH2CH3
H
H 3O
HO
CCH2COCH2CH3
O O
O
O
O
O
O
CH2CH2CH3 COCH3
CH
+
O
O
O
O
CCHCOCH
3
NaOCH
,
CH
O
O
H
,
H
O
3COCH
3OH
2
O
CCH
2 CH3CCH
3
O
2COCH3
Q) Provide the product of this reaction: + N !H
+ CH3COCH3
O
NHO
NH
2CH
2CH
2CH
2COH
CH23COH
CH2CHH
CH
CH22CH
CBr
2
2CH2CH
3 2CBr
2CH
2CH
2CH
2CCl
3CH2CHCH
2CH3CH
2CH22CH
3CH
2CH
2CH
2O
CH
CH
3CH
2CH
2CH2CH
2CCl
2CHCH
2CH
O CH3CH2CHCH
2PO
2, H
2O 2
COCH3
O CrO Cl!O
O
O
O
O
CCHCOCH
3 3 , CH2Cl2
OCCH
O 2COCH3
NH2
NH
22
NH
CH
H
,
H
3 3CH2CHCH
CH
COH
22PO
2CH
22O
H
PO
,
H
O
2CH
2CH
2
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CH
CBr
CH
CH
CH
CH
COH
2
3
2
2
2
3
2
2
2
2
3
2
2
2
2
CH
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CH
CBr
3
2
2
2
2
3
2
2
2
2
CH3
CH3CH2CH
A)2CH2CH2CH2COCCH
O Cl
CH3 2CH2CH2CH2CH2CH3
O
O
O
O
O
O O
CH3CH2CHCH
CH
COH
2 3CH
2 2CH2CH2COH
CH3CH2CHCH
CH32CH
CBr
2CH
2CCl
3CH
2CH2CH2CCl CH3CH2CH2CH
2CH2CH2CBr
CH3CH2CH2CH2CHCH
Cl
2COCCH
2CH2CH2CH2CH3
3
Cl 4
NaBH
O
O
ONaBH4, CH3CH2OHO
O
O
O O
HO
NH2
Solvent
light
h
H2PO2, H2O
Slow CCl
Fast
CH3CH2CHCH
2COH
CH3CH2CH2CH
CBr
CH
2
Q)3CH
Predict
the
product
this
3CH2CH2COH + CH3CH2CHCH
2CH2CH
2COCCH
2CHof
2CH
2CH3reaction:
3CH2CH2CCl
3CH2CH2CBr
O
H2N
H2N
BrO
O
O
O
O
O O CH3
LiAlH4
LiAlH4, (CH3CH2)2O
LDA
CH3CH2COH
CH3CH2CClCH3CH2CCl
CH3CH
CBr2 2 2CH3
CH3CH2COH
CH3
+ 2CH
CH3Cl
CH2CH2COCCH
CH32CH2CH3H22N
N
N O CH3CH2CBr
HA)
N
Br O
2N
O Br
O
O
O O
HN(CH(CHO3)2)2
Lithium diisopropylamide
PF6!
Na32COH
Cr2O7, H
2SO4, H2O
CH
CH
CCl
CH
CBr
CH3COH
3
3
CH3CBr
CH3CH2COCCH2CH3
+ CH3CCl
+O O of this reaction:
O product
O
N=N(CH3CH2)2O = N(CH3)2
Q) Predict the
N(CH3Diethyl
)2
NN
ether
+
++
BMIM hexafluorophosphate
CH+3COCCH3
H
H 3O
H2N
HO Br
Acetone N=N
)
N=N
==N(CH
CH3COCH
3N(CH33)22
N(CH
NN
N(CH33))22
Ammonia
NH3
H+, H2O
O
Acetonitrile
COC
CH3CN
+

Water
H 2O
Ethanol
DMF
CH
CH2OH
HCON(CH
)
3
+
3 2
N=N
N=N
!N(CH3)2
= N(CH3)2
N(CH3)2
Methanol
CH3OH
COC
formamide
A)
DimethylN=N
+ HCl
N(CH
)
3
2
N(CH
)
N=N
3
2
Isopropanol
!!
(CH3)2CHOH
DMSO
(CH3)2SO
Propanol
CH3CH2CH2OH
Q)Which one is the strongest base?
Dimethyl sulfoxide
Formic
acid
HCOOH
A. (CH3)2N N=N
((CH3)2N)3PO
!N(CH3)2 HMPA
CH COOH
Acetic acid

Hexamethylphosphoric triamide
Nitromethane

CH3NO2

Formamide

HCONH2

N-methylformamide

HCONHCH3

CH3CH2CH2CH2CH2CH2CNHCH3
O

CH3CH2CH2CH2CH2CNHCH3
O

=
=

CH3CCl

CH3COCCH3

+ CH
O 3NH2

CH3CH2CH2CH2CH2CH2CNH2
O
O

PCC

OH

+ ECH3OHO

CH2CH3
A)
2CH2CH2CH2COCH
3 CH3CNHCH3

CH3COCH3

O O

Q) Provide the product(s)

CH3of
COthis reaction:

2CH2CH2CH2COCH
2CH
3 2CNHCH3
CH
3CH

CH3COCH3
O

CH3CNH2

CH3CH2CH2CNHCH3
O
O

CH3CH2CH2CH2CNHCH3
O

Pyridinium chlorochromate

Q) Provide the product of this reaction:

=O

= =O =

=O

=O

=O

=O

=O

=O

=O

=O

=O

PyH+, CrO3Cl-, CH2Cl2

OCH=CH
CH
2CH2CH2CH2CNH2
CH3CH2CO
2
CH3CH
3CH2COCH3
O
CH3CH2CH2COCH2CH3
O2N
Cl O2N
Br O2N
Cl2, NaOH
Toluene
O
F
CH
CH
CH
CH
CNH
CH
3
2
2
2
2
CH
of this
CH3product(s)
CH
CH3 Q) Provide the
3reaction:
O
O
+ N !H
CCH3CH2CH2COCHA)
3
O
2CH
2CH2NH2 + CO
2
CH2CHCH3 CH3CHCH
CHCH
CHCH
3
3
NO2
NO2Cl
3CH2CH2CH2COCH2CH3 CH3CH2CH2CH2COCH3
2
CrO3Cl!, CH
CH3CH2CH2CNH2
2
O
CH
3
O
Br
NO2
CH2CH3 CH3
CH3
O
NH2
CH3CH2CH2CH2CH2CH2CH NH2
CH3CH
E 2CNH2 O22NNH
COCHCH
NH2 O2N
OH O2N
2CH
3
O2CHCH
3 3CH2CH2CH2CH2CH
COCH3 CH3CH2CH2CH2CH2CH2COCH
2CH2CH2CH3
O
O
NaBH
NaBH
,
CH
CH
CH
CH
CH
CH
CH
4
4
3CH2OH
3
2
2
2
NO
CH=CH
22
CH3
CHCH
Cl
3HO
Cl2
3CNH2
NH
NH
SO3H
O
2
2
CH3
CH3CH2CH2CH2CH2CH2COCH3
NaNO2, HCl, H2O, 0C HNO
2PO
2, H2O
NO2
2
Q) Predict the product
of this
F
CHreaction:
3CH2CH2CH2CH
CHCH2CH3
LiAlH4
LiAlH4, (CH3CH2)2O
Br
NO2
HCC CH
CH3CH2CH2CH2NH
O
COCH
COCH
COCH2CH2CH3
2
3
3
CH
Cl
3
CH
3
NO2
CH3CH2H
CH
CH
CH3
Br
2N2
O2NH2N
NHCH
O2N
Na23Cr2O7, H2SO4, H2O
A)
O
Br MgBr
CCH3
CCH2CH3
+

!
O
O
CH3CH2CH
CH3CH2NH
SO3Na
O
+
HO
H2N
CH3
H2N
Br H NO2 H3O
MgCl
CH3CH
Cl
CH2CH2OH
CO
H2O, 340C,
150 atm
H+, H2O
O

+ NaOH

=
=

+
O O !
OH
CH3CH2CH2CH2CH2CH2COCCH
2CH2CH2CH2CH2CH3
OH
CHCH3
O O
CH2NH2

=
=

butanoic anhydride

=
=

CH2NH

CH2NHCH3

=
=

A)

CH3CH2CH2CH2CH2COCCH2CH2CH2CH2CH3
O O
!
CH
CH2COCCH
Q)3CH
Draw
compound
from
2CH2the
2CH2CH
2CH3the name:
O O

A) CH3CH2CH2COCCH2CH2CH3
O O

++

=
=

!
!

CH3CH2COCCH2CH3
O product(s)
O
Provide the

of this reaction: (CH3)2CHCH2NH2

NaNO2, HCl, H2O, 0C

=O

=O

=
=

Q)
3COCCH3
A) (CH3)2CH
CHCH
2N2
COC

O2N

=O
=O

O2N

Q) Which product does not form from this reaction: NH3 + CH3Br
Br O2N
I
Cl O2NO2N
Br OCl
I
2N O2N
A. CH3NH
2
CH2OCH3
CH3
B. (CH3)2NHCOC
NO
NO2
2
NO32)3N
NO2
NO3 2 NO2
CH2OCH
C. (CH
OH
D. (CH3)4N+ Br CH2OCH3
O
N
NH
O
N
OH
O
N
2
O22N form
OH 2 O2N2
OCH3
E. all of NH
the2 product
CH2OCH2CH3 CH
3
CH
OCH
3
A) (E) 2
NO22
NO

NO2

O2N

Q)

CH2OCH3
H3C
2N
Provide
the3 Oproduct
of this
NHCH
CH3OCH2
NO2

A)(after step 1)
H2O, 340C, 150 atm

H3C

NO
NO
2 2

OCH3
NO2

OH
H3C
NH2
NHCH
3
reaction:
O2N

+ 3
CH2OCH
NN
NO2

H2O, 340C, 150 atm

NH2

Solvent
0C
2, HCl, H2O,
3
Slow
Fast
O3NaNO
OCH2CH
2N
OCH2CH
LDA
H3C
NO2 diisopropylamide
Lithium

(after step 2)
7

Diethyl ether
ofAcetone
12
Acetonitrile
DMF

OH NO2
HN(CH(CH3)2)2
(CH3CH2)2O
CH3COCH3
CH3CN
HCON(CH3)2

light

h
CH3

+ CH2CH2
N
PF6!

BMIM hexafluorophosphate
Ammonia
Water
Ethanol

Cl

CuCN,NH
KCN,

2
O

NH2

Cl

OH
OH

NH2

CH3OCH2C(CH3)2
ClHO
O

ClCH3

=O

!CH3
LiAlH4, (CH3CH2)2O

LiAlH4

CH3

CH3

Pyridinium chlorochromate
7, H2SO4, H2O
OH
OH Na2Cr2O
OH
+, CrO
PyHO
3Cl , CH2Cl2
CH3C(CH3)2 CH3CHCH3 CH3CHCH2CH3
H
H 3O +

PCC

H3C

Cl
(CH3)3CO
CuCl,
CuBr,

Cl

O HO

=
=

=O

=O

=O

=O

==

=O

!
=

OH

=O

Cl + (CH ) C

=O

HO + H!CH !CH

COC

=O

Q) Provide the key product of this reaction: CH3CH2CH2CH2CH2Br + KCN

A) CH3CH2CH2CH2CH2CH2NH2
=O

=
= =

=
=

= ==
= =

=
=
=O

=
=

=
=

Acetonitrile
DMF

CH3CN
Na2Cr2O7, H2SO4, H2O
HCON(CH3)2

Q) Rank these carboxylic acid derivatives in the order of decreasing reactivity toward
hydrolysis
(most
(CH3)2SO
HDMSO
H3O+
HO
reactive first)
A. b > a > c
B. c > a > b

CH3COCCH3

HMPA
H+, H2O ((CH3)2N)3PO
O
Hexamethylphosphoric triamide

O O

=
=

=
=
=
=

CH3CNH2

O
O
O OO O
OO O
O
CHb.
CH
2 3CCl
3COCH
3 3CH
3COCCH
3CH3CCl
CH3COCH
CH
CH3COCCH
CH
CNH
a. CH33CNH
3 CCl
2 c. CH
3COCH
3
O

=
=
=

=O

=O

=O

Cl NH2
Cl
O
Br
+
OH + N !H THF
the product(s)
of thisOreaction: CH3COCH3 + 2 CH3MgBr 1)O !
2) H , H2O
CH2CH2CH2COCHQ)
2CHProvide
3
CH3CO
CH3
NH2
Cl
NH2
CrO3Cl , CH2Cl2
O
Br
Cl
A) (CH3)3COH
CH3
CH3
CH
3 2COCH3
CH2CH
2CH
H
O
OH
O
H
O
(CH
)
CO
3
3
CuCl,

CuBr,
D
CH
CN3CH2CO
CH3CH2COCH3
NaBH4
NaBH4, CH3CH2OH
CH3
Cl
NH
2
HO
CH3CH2CH
COCH
CH
2
2
3
CN
O
OO O CH3
NaNO2, HCl, H2O, 0C CuCN, KCN,
H3C
Cl O
H3C
Br O
O
H3C
NH2
Cl
Q)CH
Predict
the
product
of
this
reaction:
OH
CNH
CH
COCH
CH
CCl
CH
3
2
3
3 O
3
3COCCH3
O
CH3CH2CH2COCH3
LiAlH
LiAlH4,
(CH3CH2)2O
4
HO
Cl
H 2COCH
CH3CH2CHCN
2CH2COCH2CH3 CH3CH2CH2CH
3
CH3
Cl
CH3
CH3
CH
3
O
CH3
Cl
Cl
Cl
A)
O
Na2Cr2O7, H2SO4, H2O
CH3CH2CH2CH2CH2CH2CNH2
CN
COCH
2CH3
O
NH2
CH CH
CH CHN(CH
CH CH
3
3)2 2COCHO
2CH3
COCH3 NHCH
Cl
Br 3 O2 2 2CN2 O
NH2
Cl
O3
H3CCH2CH3 CH3Q)
CHCH
CHCH
CH
Provide
the23CH
key
product
this 2reaction:
Br
2CH
3 2 CH
22CH
3 2CHof
3CHCH
CH
CNH
3CH
2CH
H
H 3O +
HO
O2CH2CH2CH2CH2COCH3
CH3CH
O
NH2
+
Toluene
O
Ag2O,
CH
, H2O 3)2CHCH
3I, K
22CO
2CH2CH
2CNH
Cl H22O]2AlH
CN H3HC , HH2O
CH
+ 3[(CH
Br H
H 3C H
H3C
CCH2CH2CH3 HCHCH2CH2CH
CH33CHExcess
H3C
CN
Cl
Cl
O
+
COCH
CH
COCH
COCH2CH2CH3 A) CH3CH2CH2CH
2
3
3
2CHO
O
CH3CCOH CH3CCCH3 CH3CCOH + H+ CH3CCH Cl
CH3
H3C
Cl H3C
Br
CH3CH2CH2CNH2
O
CCH2CH3
H 3C H
H 3C H
H 3C H
H3C H
H3
1) Excess CH3I, K2CO3, H2OO OH
O
CH
CH
CH
CH
CH
CH
CH
3
2
O
H 3C
2)
Ag22O, H2 2O 2 2CH3CH2CNH2
O
O
CH
CH3
CH3
O2COH
H
=O
O2N
CH2CN
O2N
CH
O
+ 3
3) H
H3CCH3
Br O
H
H+
Br! + CH3CCH
Br ofBrthis reaction:
Br
Provide
theH2CH
key
product
+ HCH +CH(CH
3CH 3)2NH
CHQ)
3CH
2CH2CH2CH
CH
CO3CNHH2
H
CH3
O
O 3)2
CH2NH
O2
OH3C H
OH CH2N(CH
OH O CH2NHCH3
Cl
Br
CN
CH3
OHCH3
H3CH
Br CH3
CH
Br
CH3CH
2CH2CH2CH
CHCN
CH3 COH
O
CH
CCH
O
3
3
CH2CH2CH2H
OH
CH3
H
O Br
O 3COH CH3CH2OH CH3COCH2CH3
=
=
= H CH
H CH3CH2CH2CH Cl
H
Cl
Cl A)
H
Cl
H3C HCCH2CH3
CN
Cl
Cl
H
H
CH3
O
O
Cl
H3CO
OH H3CO
CH3
3 2CH
OH3CO
3CH
ClCHCH
CH3 CH3
Cl
CH3CCH
O O
2CH3
OH
Br
O
OClCH CHH3CH
CH3
Cl
H 2CH2CH
H32CO
OH PCC
H3CO Pyridinium chlorochrom
NHCH
CH3CH2CH
CH2COCCH2CH2CH
2
2
2 CO
3
H
CH
CH
Pd, P(CH3)3, 100C
O O
O3
O
O
HCCH
CH
CH
2
2
3
+O
KOH
O
O
Br Q) ProvideBrthe product ofBrthis reaction: Br
PyH+, CrO3Cl-, CH2Cl2
OCH
CH
COCCH
3CH
2CH
2CH2CH2CH
2CH
2CH
2CH
3
CH3CH2CH2CH2CH2CH2COH CH3CH2CH2CH
2CH
2CH
2CCl
3CH2CH
2CH
2 2CH
2CH
2CBr
CC
CCH
3
O O
CCHO3
O
O
O
CH3CCH2CH2CH
Cl
HOH
OH H3CO OCH O
NHCH
O 3
3
3CO
3
OH
OCH23CH2CH2CH
CHCH
3CH2CH2CH2COCCH
O3
CH3CH
COH
CCH3
CH3CH2CH2CH
CH3CH
2
2CCl
2CH2CH2CH2CBr CCH3
CCH
A)2CH2CH2CH2O
O O3
!
O
O
+ N !H+ OH
3
3
CH3CH2CCH2CH3
Cl
CH
3CH2CH2COCCHCH
2CH
2CH
3 2CH2CBr
CH3CH2CHO
2CH2COH
CH3CH2CH
2CCl
3CH
2CH
O 2CH
CrO3Cl!, CH2Cl2
O
O
O
O
NHCH3
OH
O
O
O
Cl
CH
3
CCH
CCH
3
Cl
Cl3
Cl
CCH3
CHCl
3CH2COCCH2CH3 + H2O
Q)CH
Predict
the
product
of
this
reaction:
CH33CH
COOH
3CH2CH2COH
CH3CH2CH2CCl
CH
2CH2CBr
O O
!
+
O
O
O
2
2
CHCl
3
OH
OCH3
CH
3COCCH
33
OH
OCH
NaBH
NaBH
NHCH
OH
4
4, CH3CH
3
CH3CH2CCl
CH
3CH2CBr
Cl A) 2 CH3CH2COH
HO
CH
2Cl2
O
O
O
CHCl3
COC
CH3COH
CH3CCl
CH3CBr
Acetone
LiAlH4 CH3COCH
LiAlH4,
(CH3C
3

Nitromethane
N,N-dimethylformamide

8 of 12

CH3NO2
HCON(CH3)2

CH3CO

OH

CH3CH2CH2CH2CH2COCH3

CH3
Pyridinium chlorochromate

PyH+, CrO3Cl-, CH2Cl2

O
HO
CH3CH2COCH3

CH3CH2CO

=O

CH CH CH COCH CH3

+ N !H

2
C. a > c > b 3 2 2O
D. b > c > a CH3CH2CH2COCH3
E. c > b > a
A) (D)

CrO3Cl!, CH2C

CH3COCH3

PCC

NaBH4

NaBH

LiAlH4

LiAlH

O 2Cl2
CrO3Cl!, CH

=O

=O

Q) Cl
Provide
the key product of
reaction:
H3CO
OHthis
H3CO
A)
CH3CH2CH2CH2OH
CH2HCH
H3CO
NHCH3
3CO
2CH2OH

=O

COCH3

HO

Na2Cr2O7, H2SO4, H2O

O
O
O
O
NH2 , CH CH OHNHCH3
N(CH3)2
NaBH4
NaBH
4
3
2
+
CH3CH2CH2CH2CH
2COCH2CH3
H
H
O
3
CH23CH
CCH
CH
CH
CHCH
CH
CH
CHCH
CH
CH
2
3
3
2
3
3
2
3
3CHCH2CH
HO
O
O LiAlH4
NH
2
H+, H2O
LiAlH
4, (CH
O3CH2)2O
CH3CH2CH
2CH23CH2CH2COCH3
A
Excess
CH
NHCH
3I, K2CO3, H2O
HCCH CH CH HCHCH CH CH

=
=

=O

=O

3
CH3CH2CHCH
2CH2COCH2CH3 CH3CH2CH2CH2COCH3

COCH2CH3

Cl

CH3CH2CH2CH2CH2COCH2CH3
O

H3CO

OH

=O

O Na2Cr2O7, H2SO4, H2O

COCH2CH3
COCH3
COCH2CH2CH3
Pd, P(CH3)3, 100C
HCCH2CH3
O O O
O
O
1) Excess CH3I, K2CO3, H2O
Pd, P(CH3)3, 100C
+
H
HO
3O
CCH3
CCH3
O
O
2) Ag2O, HPCC
HO
2O
CCH3
Pyridinium chlorochromate
3)

CH
CCH
CCH
CCH
3
3
3
3
+, H O
H3
H
2
Q) Provide the product(s) of this reaction:(CH3O
)2CHCH2CH2CH2CH2NH2
PyH+, CrO3Cl-, CH2Cl2
O
NHCH
OH
3
Cl
A) (CH3)2CHCH2CH2CH=CH2 + (CH3)3N CO
CH3CH
NHCH3
OH
Cl
O
+ N !H
O
O
COH
H3CO
NH2
CCH3
CrO3Cl!, CH2Cl2
O2N
CH2CN
O2N
CH2COH
CH
3
Pyridinium chlorochromate
PCC
H3CO
O NH2
+, CrO
2CH
CH2CN
O2N
CH2COH
PyHOCH
3Cl3, CH
O2
NH2
OH
OH2Cl
O
O reaction:
O
Q)
Provide
the
product
of
this
+
HI

NaBH4
NaBH4, CH3CH2OH
NH2
CHCN
CH COH
HO
COH
COH
O
O
CH
CH
CH
CH
CH
CH
CNHCH
3
2
2
2
2
2
3
OH O
+ON !H
COH
COH
N
CH COH
LiAlH4
LiAlH4, (CH3CH2)2O
CH3CH2CH2CH2CH2CNHCH
CrO33Cl!, CH2Cl2
OH
OCH3
O
CH3
OH
OCH3 CH CH CH CH CNHCH
Na2Cr2O7, H2SO4, H2O
3
2
2
2
3
A)
+ CH3CH2I
O
O
O
NaBH
NaBH4, CH3CH2OH
4
O
O
O
HO
CH3CH2CH2CNHCH3
H
H 3O +
HO
O
CH3CH2CH2CH2CH2CH2COH CH3CH2CH2CH2CH2CH2CCl
CH3CH2CH2CH2CH2CH2CBr
OCNHCH
O
LiAlH
O
H+, H2O
LiAlH4, (CH
O
4
O
O CH3CH
3CH2)2O
O
2
3
Q) Provide the key product of this reaction:
O
3CH
2CH
2CH2CH2COH
CH3CH2CH2CH2CH2CCl
CH3CH2CH2CH2CH2CBr
CH2COH CH3CH2CH2CH2CH2CH2CCl
CH3CH2CH2CHCH
2CH
2CH
2CBr
A) CH3CH2CH
O
O
O
O
O 2NHCH3
O
CH
Na32CNHCH
Cr2O7, H32SO4, H2O
CH
CH
CH
CH
COH
3
2
2
2
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CBr
3
2
2
2
3
2
2
2
CH2COH
CH3CH2CH2CH2CH2CCl
CH3CH2O
CH2CH2CH2CBr
O
O
O
O
O
OO
O
+
O
H
H3O
HO
CH2COH
CH
CH3reaction:
CH2CH2CHCH
Q)3CH
Predict
the
product of this
Cl
3CH2CH2COH + SOCl2
CH3CH2CH2CCl
CH3CH2CH2CBr
2CH2CH
2CCl
2CBr
O
O
O
O
O
HO+, H2O
O

=O

!
=

OH

Cl

OH

OH

Br
OH

OH

OH

Br

OH

OH
OH

OH

OH
OH

OH

OH

CH3CBr
Cl

Cl

OH
+ HBr

! ! !

OH

A)

OH

! ! !

OH
OH
O

Br

OH

! !
=

Br

CH=CHCH2CH2CH=CH2

Br

OH

CH3CCl
OH
O
Cl

CH=CHCH2CH2CH=CH2

=
! = !

Q) Predict the finalOOH

product of this conjugate addition reaction:
CH2=CHCHCH2CH=CH2

O
O

CH3CH2CBr
O

! = !

CH2=CHCHCH2CH=CH2

= =

CH3COH

CH2COH
O

CH3CH2CCl
O

CH3CH2CH2CBrCH3CH2COH
O
O CH =CHCHCH CH=CH
OCH=CHCH
2CH2CH=CH2
2
2
2
CH3CH2CCl
CH3CH2CBr CH3COH
O
O
O
OH
Br
CH3CCl
CH3CBr
O

CH2COH
O

=
=

=!=

A) CH3CH2CH2CCl

=O

!
==

OH

9 of 12

Cl

=O
CH3CCl

=
= =

CH3COCH3

CH3CNH2

!, CH4 Cl
CrO3ClLiAlH
2 2

O O
CH3
CH3COCCH3

Cl! + (CH3+)3NC!H+

Na2Cr2O7, H2SO4, H2O

!
+
HO
O + H!CH2!CH2
NaBH4
H

AcetoneO

Q) Provide the key product of this reaction:

CH
3CH2CH2Br + NaN3
CH3CH2CH
2CH2CH2CNH2
O
A) CH3CH2CH2NH2

O
HO
CH3CH2CH2CH2CH2CH2CNH2 HO
O

DMF

=O

=O

CH2OCH3

Acetonitrile

CH3CH2CH2CH2CNH2
CHO
O
3

(CH3)3

LiAlH4, (CH

NaBH4, CH3CH2OH

H3O+

LiAlH4 CH3COCH
H+,LiAlH4,
H2O
(CH3CH2)2O
3
CH3CN
Na2Cr2O7, H2SO4, H2O
HCON(CH3)2

(CH3)2SO
TolueneH3O+
HDMSO
HMPA
H+, H2O ((CH3)2N)3PO

Iso

=
= =

= =
=

=
=
=
=

=
= =

=
=

!
=

=
= =

!
=

=
=

=
=
=O
=O

=O

!
=

=O

=
=

=
=

=
=

=
=
=

=O

!
=!

= !=

=O

=
!

= !

=O

=
=

=
= =

=O

CH3CH2CH2COH
CH3CH2CH2CCl CH3CH2CH2CH2CBr
CH3CH2CH2CBr
CH3CH2CH2CH2COH
CH3CH2CH2CH2CCl
O
O
O
O
O
O
COH
CH3CH2CCl
CH3CH2CH2COHCH3CH2O
CH3CH2CH210
CClof
CH3CH2CH2CBr CH3CH2CBr
12 O
O
O
O
O
CH
COH
3
CH3CCl
CH3CBr
CH3CH2COH
CH3CH2CCl
CH3CH2CBr
O
O
O

P
Cl2, NaOH
CH3CHHO
2CH2CNH2
O
Fo
OH
O
CH3CH2CNH2
A
O
Hexamethylphosphoric triamide
O
CH3
3
CH2OCH2CH3CHCH
Fo
CH3CH2CH2CH2CH2CH2CH 3
CH2OCH3
CH3CNH2
CH3NO2
Nitromethane
O2CH
O3CH
2CH2CH2CH2NH
O CH
N-me
3CH2CH2CH2CH2CH2CNHCH3
OCH2CH2CH3CHCH
2CH2CH2CH2CH OCCH2CH2CH3
N,N-dimethylformamide
HCON(CH3)2
OH
O
CH2OCH3
O
OH!, H2O
CrO
CH
3, 2H
2SO4, H23O+ CH CH Br
2OH
O
CH
CH
CH
CH
CH
CNHCH
Q) Provide the product of
this
reaction:
3
2
2
2
3
2
CH3CH2CH2CH2CH
H3C3 H
Br H
H3C CH
H3
HO3C
H3C
CH
O2N
O232CH
N 2NH
CH2COH
2CN
3CH2CH
O
CH3CH
CHCH
PCC,CH
H
2MgBr, (CH
2Cl2
+ CH2)2O+
+2CH
CH3CH2+CH
2CNHCH
CH3CCOH CH3CCCH3 CH
CH
H
3CCOH
3CCH3 CH3CCH
CH
CH
CH
CH
O
3
2
2
CH3OCH2
CH2OCH3
O
O H3C
OOH
H 3C H
H3C 2CH
H3
H3C2CH
H3OH H
H
OCH
OCCH
3C
OH3C H OH
CH
3CH2CH2CNHCH3
CH3CH
2CH
CHCN
CH
COH
CH
H3C
A)
O
!LiOCH3CH2NH
+
!
(CH3CH32)2O
Br + CH3CCH
CH3CHCH3CH2CNHCH
H
Acid
Base
FeBr3 FeCl3
AlBr3
AlCl3
O O
O
O
H
C
H
3
O
OCH3
H 3C
OCCH3
3C
H2SO4, 100C
CH CNHCH
3 + H2O
Q)HProvide
the key product
Oof this reaction
CH3COCH3 3
CH2COCH2CH3
CH3CO
O
O
O
O
COH
O
CH2 33CH2CH2CH2CH2CH2COCCH2CH2CH2CH2CH2CH3
CH2NH
3CH
2OH
2CH
A) CH3COH (+CH
CH
CH2NH
3NH
2) CH3COCH
CHO
2NHCH
CH2COCH3
O 3
H
O
O
O
OO
CH
CH
CH
CH
CH
COCCH
CH
CH
CH
CH
O
3
2
2
2
2
2
2
2
2
3
CH
CH
CH
CH
CH
CH
COH
3
2
2 CH
2 CH
2 COCH
2
CH CH2CH2CH2CH2CH2CCl
CH3CH2CH2CH
O
CH3CH2CO
3
2
3 H3C3 CH
O 2CH2CH2CBr
3O O
O
O
O
O
CH2COCH2CH3
H
C
3
CH2=CHCOCH2CH3
CH3CH
CH22=C!C=CH
CH2CH2COCCH
2CH2CH2CH3 + CH3CH2OH
Q) Predict
of 3this
reaction:
O
OHthe product(s)
BrCH
CH
2=CH!CH
CH2CH
2CH2CH2COH
CH3CH22CH
CH3CH2CH2CH2CH2CBr
2CH
2CH2CCl
O
O O
O
O
O
O
O
CH2COCH3
Cl
H3C
COCH2CH3
CH CH2CHCH
2COCCH
2CH
2CH
3
3CH
2CH
2CH
2COCH
3CH
2CH
2CH
2COH3 3
A) CH3CH2CH2CH2COCH2CH3 +CHCH
CH CH
CH
CCl
CH3CH2CH
2CH2CBr
O3 O 2 2 2
H3C
O
O
O
O
CH3CH2COCCH2CH3
CH3CH2CH2COHCl
CH3CH2CH2CBr
O CH
O 3CH2CH2CCl
2CH3
H3C
COCH3 CH3CH2CH2CH2CH2CH2COCH2CH3 O
O
O
O
O
CH
COCCH
O
O
3
3
OO
CH3CH2COH
CH
CH
CCl
CH
CH
CBr
Cl 3 2
3
2
Cl
C
O
O
O O
CH3CH2CH2CH2CH2CH2COCH3
COC
CH3CBr
O2N
CH2CNCH3COH
O2N
CH2CH
COH
3CCl
COCH
CH
COCH
CH
CH
O
3 CH2=CHCHCH2CH=CH32
2
2 CH=CH
3
CH=CHCH2CH2CH=CH2
CH=CHCH2CH22CH=CH
CHCH
2
2
2
OH
Q) Predict
the product(s)
of
this
4+2
reaction:
+ O OH
O2N
CH2CN
O
O
OH
OH O CH
2N cycloaddition
2COH
COC
O
OH
OH
Br
CHCN
CH COH
Br
OH
OH
OH
OH O
Cl
Cl
CHCN
CH COH
CO
OH
OH
OH
A)
OH
OH
OH
Br O
O
O
Br
CHthis
CH2COH CH3CH2CH2CH2CH2CH2CCl + HCH
3CH2CH2of
2CH2reaction:
Q) Predict theCH
product
2CH2CH2CH2CH2CBr
2O3CH
O
O
O
O
O
O
CH2CH
3CH
2CH2CH2CH2COH
CH2CH
CH2CH
3CH
2CH2CH2CH
3CH
2CH2CH2CH2CBr
A) CH3CH2CH2CH2CH
2COH
CH3CH2CH2CH2CH
CH23CCl
CH2CH2CH2CH
2CCl
2CBr
O
O
O
OOH
O
O
CH3COH
CH2CH2CH2COH
CHCCl
CHCBr
3CH2CH2CH2CCl
3CH2CH2CH2CBr
CH3CH2CH2CH2CH
2
CH3CH2CH2CH2CH
CH3CH2CH2CH2CH
2
2
O
O
O
O
O
O
CH reaction:
Q) Provide the product(s) of
CHthis
2OCH
3
A) CH
CH23CH2NH2 + CO2
CH32OCH

+
O N !H

CH3CH2CH2CH2CNHCH
33Cl!, CH2Cl2
CrO
CH2CN
O2N
CH3
O

O2N

CH2COHCH3

H3

NaBH4

NaBH4, CH3CH2

LiAlH4

LiAlH4, (CH3CH2

O+

H+, H2O

Na2Cr2O7, H2SO4, H2O

!, CH
LiAlH4,
(CH
CrO
3CH
2)2O
3Cl
2Cl2

Na2Cr2O7, H2SO4, H2O

!=
=
=

Na2Cr2O7, H2SO4, H2O

A) CH3CH2NHCH
3
O

Q) Provide the product of this

HO

CH3CH2CH2CNHCH3
OH
OH
O O O
O
HO, CH3CH2OH
NaBH4
NaBH
CHCNCH3CH2CNHCH3CH COH 4
H
HO
O
LiAlH4, (CH
4
O 3CH2)2O
3CNHCH3
reaction: CHLiAlH

LiAlH4

= =

=O
=O

=O

=O

=O

=O

!
=

=O

= =

!
=O

=O

=O

=O

HO + H!CH !CH
=O

=O

(CH ) CCl

Cl + (CH ) C

=O

=O

=O

=
=

= = = = =
= = = =

OH

=O

==

=O

=O
=O

O H3

=O

CH2OCH3HO

H
H 3O + O
O
HO
CH
3
O
CH3CH2CHO2CH2CH2CH2COH
CH
CH2CH2CHH2+CH
3CH2CH2CH2CH2CH2CCl
, H22CBr
O
H+CH
, HCH
2O
O3CH2Toluene
O
CH
CH
3COCH
3 + [(CH
CHthis
Q)
Provide
the product(s)
reaction:
2OCH
3
O
Pyridinium
3)2CHCH
2]2AlH
2CH2CH2CH2COCH
2CH
3
O chlorochromate
O
PCC
CH3of
CO
O
CH32OCH
OH
A)
CHO3 Cl2, NaOHCH3CH2CH2CH2CH2COH CH2BrCH3CH
CH
CH3CH2CH2CH2CH2CBr
CHCH
2CH
2CH2CH
+, CrO
- 2CCl
Cl2, NaOH
PyH
3Cl , CH2Cl2
O
CH2Br
O
O
2CH2CH2CH2COCH3
O
O
O
CH
3 3MgBr, (CH3CH2)2O
Toluene CH
CH
OCH
CH
2
2
3
CH
CH
CH
COH
3
2
2
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CBr
3
2
2
2
3
2
2
2
CH3MgBr,CH
(CH
CH3
O 3CH2)2O
CH
CH3CH
3CH2CH2CH2CH2CHCH
2CO
O 2OCH3
O 2CH3CH2COCH3
O
O
O
CH CH CH COCH2CH3
OCH2CN
+ N !H
CH2CN
H2CH3 2CH2 2CH2O
CH
CH
CH
COH
3
2
2
CH3CH2CH2CCl
CH3CH2CH2CBr
OCH2CH2CH3
OCCH2CH2CH3
O 2CH
2CH
2CH2CH2NH
O
O CH3CH2CH
, CH2Cl2 !
CH
OCH3CH2CH2CH2CH
O OH CrO3Cl!O
2OCH3
HCH
3CH
2CH
2COCH3
2CH
2CH
2NH
O
OH , H2O
CH
3CrO3, H2SO4, H2O
CH
OH
2
CH
CH
COH
H2CH2CH2CH
3
2
CH
CH
CCl
CH
CH
CBr
3
2
3
2
Q) ProvideCH
the
product
of this2CH
reaction:
3CH
2CH2CH2COCH
3 CH3CH2CH
2CH
2COCH3 +
CH
2CN
O 2CH
O
O
CH3CH2CH2CH
O
CH3
CH2CN
CH
CH
MgBr,
(CH
CH
)
O
PCC,CH
Cl
H
3
2
3
2
2
2
2
O
CHO3COH
CH3CCl
CH3CBr
H2CH2CH2CH
O 2OCH3
!
NaBH4 +
NaBH4, CH3CH2OH
CH
3OCH2
COCH2CH
CH
3
HO
3
3
3
3
CH
CH
CH
CH
CH
CH
COCH
CH
CH
CH
CH
CH
CH
CH
CH
CH
NH
3
2
2
2
2
2
2
3
COCH
3
2
2
3
2
2
2
O
3
H3C
OH
CH
2NH2CH3
OCH
OCCH2CH3 O
O CHO2CH2NH2
CH2CH2NH2
H3CH2CH2CH
CHCH CH CH
LiAlH4
LiAlH4,
3CH2CH
O A)
CH3CH2CH
!
+ (CH3CH2)2O
2
2
2 CH
2COCH
3 !Li
2
2
2
2
2
O
(CH3CH2)2O
CH3CH2CH
H
O
CH
CH
2
CH3CH2NH
3CH2)2O
CH2Diethyl
CH2NH3ether
O
3COCH
COCH
Na2Cr2O(CH
key
2CH
3 of this reaction:
2CH2CH3 Q) Provide the
7, H2SO4, H2O
2N
3
CH
CHproduct
2COCH
2NH
2
HH2NH
OCH
H
OCCH
3
3C
3
Acetone
CH3CH
O
OO
CH3COCH3
+
COH
HCH Br
H 3O
Acetonitrile
CH3CN
CH2HO
NHCH3
2
Water
H2O
CH2Br
!, H O
+
H
CH2NH2
Ethanol
OH
2
CH3CH2OH
H , H2O HCON(CH3)2
CrO3,O
H2SO4DMF
, H2O
CH2OH +
Methanol
CH3OH
CO
CH3CH2MgBr, (CH3Dimethyl
CH2)2O formamide
PCC,CH2Cl2
H
CH2NHCH3
Isopropanol
(CH3)2CHOH
CH2NH2
CH2N3
DMSO
CH2NH
(CH3)2SO
CH
2NH
Propanol
A)
CH3CH2CH2OH
O
Dimethyl sulfoxide
Formic acid
HCOOH
CH
!Li
HMPA
O
O
((CH3)2N)3PO
O
CH
Acetic acid
3COOH
(CH
3CH2)2O
H
CH
3COCH3
2CH2CH2COCH2CH3
CH3CO
Hexamethylphosphoric triamide
Formamide
HCONH2
O
N-methylformamide
HCONHCH3
O
CH3NO2
Nitromethane
2CH2CH2COCH3
Solvent
h 2CH2light
CH=CHCH
Slow
Fast
O
CH=CH
CH
=CHCHCH
CH=CH
2
2
2
2
O
Q) Provide the product
COH of this reaction:
O
HCON(CH3)2
CH3CH2CO
CH3N,N-dimethylformamide
CH2COCH3
LDA
H
3CH2CH2COCH2CH3
CH3
+ CH2CH2CH2CH3
N
N
O
HN(CH(CH3)2)2
O
Lithium
diisopropylamide
PF6!
O
O
3CH2CH2COCH3
CH2CN
O2N
CH2COH
CH3CH2CH
2CH
2COCH22CH3 CH3CH2CH2CH2COCH
CH=CHCH
CHCHCH2CH=CH2A)
O (CH33CBr
2CH
2CH=CH
CH2)2O
Diethyl ether
BMIM hexafluorophosphate
CH
CH
CH
CH
CH
CNHCH
3CH
2
2
2
2
2
3
O
Acetone
OH
OH O
CH3COCH3
O
Ammonia
OCH2CH3
NH3
CH3CH2CH2CH2CH2CHCOH
2COCH2CH3
COCH
CHCN
CH3 COH
Acetonitrile
CH33CN
CH
3CH
Water
O2CH2CH2CH2CNHCH
H 2O
CCl
O
Ethanol
DMF
CH3CH2OH
CHthis
CH2COCH3
HCON(CH
3CH2CH2of
2CH2reaction:
3)23CH2OH
Q) Predict theCH
product
+ CH
CH3CH2CH2CH2CNHCH3
Methanol
CH3OH
Dimethyl formamide
O
CCl
CBr3
COCH2CH
COCH3
OCH2COH
CH2CH3
Isopropanol
(CH3)2CHOH
CH3CH2CH2CNHCH
3 ) SO
DMSO
(CH
3 2
A)
O
Propanol
CH3CH2CH2OH
Dimethyl sulfoxide O
O
O
CH3CH2CNHCH3
Formic acid
HCOOH
O ((CH
HMPA
CH2CH2CH2CH2COH CH3CH2CH2CH2CH2CH2CCl
CH
3CH2CH2CH2CH2CH
2CBr
3)2N)3PO
CH
Acetic
acid
3COOH
O
O this compound: CH3CNHCH
O3
Q) Provide the name
for
CO
Hexamethylphosphoric triamide
Formamide
HCONH2
CH2CH2CH2CH2COH
CH3CH2CH2CH2CH2CCl
CH3CH2CH2CH2CH2CBr
O
O
O CH NO
N-methylformamide
HCONHCH3
Nitromethane
3
2
CH3CH2CH2CH2COH
CH3CH2CH2CH2CCl
CH3CH2CH2CH2CBr
(CH3)3COH
tert-butyl alcohol
O
N,N-dimethylformamide 11OHCON(CH
O
of 12 3)2
CH3CH2CH2COH
CH3CH2CH2CCl
CH3CH2CH2CBr
O
O
O
CH3CH2COH
CH3CH2CCl
CH3CH2CBr
O

O+

H O + H C=CH

CH3
CH2CHCH3

CH3
A) N-methylethanamide

CH3

CH3

CHCH3

CHCH3
CH3

NO2

CH3
CH2CH2CH2CH3
O

=O

=O

Q) Which OCH
carboxylic
the best
leaving
group?
O
OCCH
OH
O
O
2CH2CH3acid derivative
2CH2CH
3
CH3 has
A. amide
HCCH2CH2CH2CH3 HCCH2CH2CH2CH2CH3
CH3CCH2CH2CH2C
CHCH2CH3
B.
acyl
halide
O
O
O
O
CH3
CH3
C. anhydride
=O CH3CCH2CH2CH2CH2CH
HCCH
O
MgBr2CH2CH2CH2CH
CCH3
CCH2CH3
D. ester
O
O
OCH2CH3
OCCH2CH3
HC=O
E. acid
CH=CH2
HCCH2CH
CH3
H MgCl
CH
A) (B)
CH2CH2OH
O

OCH3

H3C

H 3C
OH

CHCH+
3

OH
CH

OH

3Br2

CHCH3

=O

OCCH3 O2N
CH
3
OH

=O

Q) Provide the product(s) of

CH3
CHCH3
this
CHreaction:
2CHCH3

C=C
CH3CH2
CH2CH3
Pyridinium chlorochromate
PCC

CH3

CH3

PyH+, CrO3Cl-, CH2Cl2

O
CH3
O
O
H
+ N !H
Br
H
CH2CH2CH
2CH3CH3CH
H CH
Br
HCH
H
C
OH
3
NO
3
2
Br
OH
H
H
CH3
CrO3Cl!, CH2Cl2
O
O
O
CH
3
CH3
OCH3 CH3
Br CH3
Br
Pt
H2, Pt
CH3CCH3
OCCH2CH2CH3 Br
OH CHCH
H3
BrA)
H
H 2CH3OBr
PtO2
H2, PtO2
NaBH4
NaBH4, CH3CH2OH
Cl
H
H
HO Pd, C
H
Cl
HCCH2CH3
H2, Pd, C
H
H
CH
3
O
NaOH, H2O, pressure
CH3
MgBr
CCH3O
CCH2CH3 Raney Ni H2, Raney Ni
CH3
LiAlH4
Cl CH3
CH
Cl of this reaction:
LiAlH4, (CH3CH2)2O
3
CH3CCH2CH3 + CH3NH2
Q) Provide
the
product
O
O
H3
NH2 Cl
NHCH3 HCH3 N(CH3)2
CH3
NO2
OCCH2CH3
H
H3 CH3CHCH2CHA)
3 CH3CHCH2CH3 CH3CHCH2CH3
Na2Cr2O7, H2MgCl
SO4, H2O
HCCH
2CH2CH3
O
Br
Br
Br
CH2CH2OH
O
O
NH2
NHCH3
N(CH
)2 2CH3
OCH23CH
OCCH2CH2CHO3
OH
CH
CCH
CH
CH
3
2
2
3
CH
HCHCH
CH
CH
HCCH
CH
CH
HCCH
CH
CH
H
H 3O +
2
2
3
2 O 2 OCH
3
2
2
3 OCH
OH 3
OH 3
3
OH
HO
O
OH
NH
NHCH
H3C
OCCH
O2N(CH
N 3)2
OH
2
3
CHCH
NaOH, H
3 CH3
H+, H2O
CH3 3
O2O, pressure
CH
3CH2CCH2CH3
Q)
Provide
the
product(s)
of
this
reaction:
+ CO2
HCCH2CH3
HCCH2CH3
HCCH2CH3
O
O
NHCH3
N(CH
)2
ClNH2
Cl
Cl 3CH
OCH
OCCH
2
3
O
O 2CH3
CH3COOH
CH3CCH3
CH3CCH3
CH3CCH3
CONa
COH
CHCl3
OH
OH
NH2
NHCH3 OCH3 N(CH3)2 OCH3
CH2Cl2
H3C
OH
O
CH3CH
CH3CH
CH3CH
CHCl
3
OH
OH
HC
OCH
HC
OCCH
ON
OH
Br

=O

!
=

=
!

=O

=O

A)(after
step 1)
Br

(after step 2)

Br
Br

OH
Br

H 3C

OH
Br

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