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Exam II
Practice Exam
Chem. 212
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1 of 10
Q)Write the base catalyzed product(s) for chlorination of cyclobutanone
=O
A)
Cl
Br
Cl
Br
H
H
Br
=O
H
=O
Br
Br
H
H
=O
Cl
Cl
H
Br
=O
=O
Cl
H
H
H
H
=O
Br
H
NO2
=O
Q) Provide an
Cl IUPAC name
Br for this compound:
Br
Cl
Br
H
H
A) 2-nitrobenzoic acid
NO2
Cl
CHO
=O
Br
Cl
COH
Cl
H
=O
Cl
=O
Q) Select theClbest answer for
the effect of Ha chloro (-Cl)H substituent
on benzene for electrophilic
COH
Br
aromatic substitution
=O
=O
=O
=O
A. activates the ring and directs ortho/para
Cl
Cl
B. deactivates
the ring and Br
directs meta Br
Cl
Br
OH
COH
2N
C. activates
the ring and
directs metaH
D. deactivates the ring and directs ortho/para
E. no net activation and directs to ortho, meta, and para
A) (D)
H
: !
Q)Provide
the product of this reaction of 3-chloropropanal:
!
ClCH2CH2CHO + 2HNO3 →
!CR !NHCR !COR !COH
A) CH
ClCH
H (+ 2NO2 + H2O)
2CH
CH23CO
CH22CCl
3CCl
=O
=O
=O
=O
=O
=O
=O
=O
3COCCH3 CH
2CCl
HCCl CH
Q) Which
compound
has3CH
the2CH
smallest
pKa?
=O
OCCF3
=O
=O
=O
H
:
H
=O
CH3
A. HCOH
B. CH3CH2OH
OCCF3 O
O
H
OO
O
HO
CH
HCH
CH3CH
C. HCH
HCH
CH33CH
CH
CH3
H
O
O
O
H
O
O
O
H
CH33
CH
rr
C(CH3E)+3
H
E
E
+
H
E
CH
D.
CH
3CCH
+ 33
+
CH33CCH
CCH
H
CF3
HO
CF3
CF3 O
O
H
H
H HCCH
HCCH
2CH3 22CH
CH33
E. HCCH
H
O
H
H
O
+
H
O
A)
(A)
E
E
E
OE+ O
O3CCH
CH
CCH
CH
3 22CH
+
CH233CH
CCH
CH33
+
O
O
O
H
H
Select
the resonance
structure of the
that most destabilizes electrophilic (E+) attack of
HQ)HCCH
CF
CFintermediate
33 2CH3
3
CF3
22CH
HCCHHCCH
2CH2CH
CH
2CH3
O
O (trifluoromethyl)benzene
at the para position. Lone pairs of electrons are not shown in the diagrams.
O
H
3
CH33
CH
Br
Br
CF3
H
H
CH
CCH
22CH
3
CH
3CCH
2CH
3 22CH
CH23CH
CCH
CH
CH
E 3
OCH3 OCH
E+ 33 O3
OCH
O
O+
CF3
A.
CF3
CH
CCH
33CH
CH3CH
2CCH
3 22CH
CH
CH22CH
CCH
CH33
Cl
Cl
O
+
H
E
CF3
+
H
E
CF3
O
O
Electron
withdrawal by induction
CH COOH
CH3COOH
CH33COOH
CHCl3CHCl
CHCl33
OCH3 OCH
OCH33
CH2ClCH
2
CH22Cl
Cl22
CHCl3CHCl
CHCl33
2 of 10
+
H
HE
E+
3
+
CF3
CF3
+
H
HE
+
E+
+
CF3
CF3
+
+
H
HE
E+
CF3
CF3
H
C.
CF3
CF3
H
EH
E
+
+
E+
CF3
+
=O
CF3
CF3
O
H
EH
+
(CH3)3CO
CF3 H
E
+ CF3 H
O
+
+
onCF withdrawal by induction
(CH ) CO
CF
CF by induction
D. CFwithdrawal
Electron
H
H
3
3 3
3
H
H E
E+
+
H
E
H
+
O E
!
3Cl , CH2Cl2
H2SOCrO
4
CH3
CH3
H
E
+
H
+ N !H
OH
CF3
E
CF
3
+
PyH+, CrO3Cl-, CH2Cl2
H
E
+
O HO E
NaOH
NaBH4O
O
3
3
E
H
E
NaBH4, CH3CH2OH
!CH3
LiAlH4, (CH3CH2)2O
LiAlH4
+
CF3CH3
Pyridinium chlorochromate
PCC
OH
H
EH
E
+
HHO
H
E
E
CF3
CF3 H
E
H
E
+
E
+
CF3
CF3
B.
H
EH
+
H
EH
E
H
E
+
+
!
!
=
=
=
+
OH
=
CF3
=
E.
A) (E)
E+
=
, H2SO4, H2O
OH
OH Na2Cr2O7OH
O
O
CH3OCH2C(CH3)2
CH3C(CH3)2 CH3CHCH3 CH3CHCH2CH3
CH
3
O
H
H 3O +
H
H
+3
H
CF3
CF3
CF3
HO
CF
E
E
E
+
O2N
CH2CN
O2N
CH2COH
+
OH
THF
+
H+ Q) Provide
H2Li + CO2 O
+ 3CH
H
O
theHproduct Oof this reaction:
CH
1)
2) H , H2O
CH3
E
+
E
CH2COH CF EA) CH3CH2+COE2H
OH
OH O
+ CF3
3
CF3
CF3
CHCF
CF3
3 3
CF3
CHCN H
CH COH
OH
H
+H
H
H
CH3
NO2
(CH
3)3CO
D
E
+
E
E
CH3
+
+
O
CF3 CH3
CF3
CF3
OH
CH3 HOOC
CH3
H 2N
HO
Q) Which answer best explains theHresult from nitration of this compound
CH3
CF3
Electron withdrawal by induction
ectron withdrawal
by induction
A. nitration occurs predominantly ortho to -NO2
Cl! + CCH
(CHCH3)3C+
2
HO + H!CH2!CH2
CHCH3
OH
H ether
Diethyl
Acetone
OAcetone
H2O + H2C=CHDMF
2
DMF
OCH2CH3
Acetone
CH3COCH
3
Q)Predict
the product(s)
of this
reaction:
Acetonitrile
=
=
=
=
=
=
=
=
=
=
=
=
MgBr
Q) Provide the product of this reaction: CH3CH2Br + KCN 1)
2)
Acetonitrile
MgCl
Acetonitrile
A) CH!3CH2CO2H
CH2CH2OH
+
OH
=
=
=
(CH3)HO
3CCl
3
CH3CN
DMF
HCON(CH3)2
DMSO
(CH3)2SO
HMPA
((CH3)2N)3PO
Hexamethylphosphoric triamide
(CH ) CCllig
HO + H!CH !CH
=
=O
C6H5CCH(CH3)A)
2 C6H5CC(CH3)3
CCH3
=
=
O
=
=
=
Q) Provide the product
CHCH2CH3
O
3
Cl + (CH ) C
CH3CBr
=
CH3
=O =
CCl
O
CrO3Cl!, CH2CH
Cl23CH2CH2CBr
CH3CH2CH2COH
CH3CH2CH2CCl
CH3
CH
3
O
O
O
CH3
C(CH3)3
H3C
CHCH
3
CH
CH
COH
3
2
CH
CH
CCl
CH
CH
CBr
of this reaction: 3 HO
3
2
C≡N + PBr3 →
CH33O 2O OCH3
O
O
CH3
NaBH4
NaBH4, CH3CH2OH
HO
CH
3COH
CH3CCl
CH3CBr
CH3+
OCH3
!
3hν3
Solvent
Δ
Slow
Fast 3 3
LiAlH4
LiAlH4, (CH3CH2)2O
O
O
CH3
Very fast
LDA
Very slow
6H5CC(CH
3)3
CH3
of this reaction: C6H5CCH(CH3)2 +CCH
3I
N
Na
Cr
O
, H2SO4, H
2
2
7
!
+32)O
LiN(CH(CH
)
Lithium diisopropylamide
2
2
2
2
2
O
O
=
=
=
=
=
=
CCl
A) 3 CH3CH2CBr CH O
C≡N
HOCH2CH
3
O
O
2CH2CH3
=
=
2
CCl
CH3
CH3CH3CH2CH2CH2CBr
O HN
O
CH3 HOOC
2
CH2CHCHQ)
CHCH3
3 Provide the
CCl
CH3CH2CH2CBr product
O
O
=
=
CCl
O
=
=
CCl
O
O
B. nitration occurs predominantly
ortho to -CH
Pyridinium
chlorochromate
PCC
CH3CH2CH2CH2CH2CH32COH CH3CH2CH2CH2CH2CH2CCl
CH
3CH2CH2CH2CH2CH2CBr
OH
O
O
O
C. nitration occurs
predominantly ortho to -COOH
O
PyH+, CrO3Cl-, CH2Cl2
CH
CH
CH
CH
CH
COH
2 to
2 -CH
2
CH3CH2CH2CH2CH2CH
CBr3
D.2CH
nitration
occurs predominantly 3meta
CH3CH2CH
32
2CH2CH2CBr
CH3 CH3CH2CH2CH2CH2CCl NO2
O
O
O
O
E. nitration occurs predominantly para to -NO2
CH
CH
CH
CH
COH
3
2
2
2
=O
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CBr
3
2
2
2
3
2
2
2
CH3CH2CH2CH2CH2CBr
+ N !H
A)CH
(B)
NO2
3
O CH3
O
O
O C(CH3)3
CH3 HOOC
CH3
HN
HC
=
=
O
O
H3C
Water
Ethanol
NH2
+
Methanol
Formic acid
Acetic acid
H+, HCH
O 33COCH
2CH
COCH33
CH
CH33CN
CN
HCON(CH
HCON(CH3)32)2
DMSO
Dimethyl formamide (CH3)2SO
H2O
HMPA
((CH
3Br2 DMSO
(CH3)32)N)
3PO
2SO
CH3CH2OH
Dimethyl sulfoxide
Hexamethylphosphoric
triamide
CH OH
3
HMPA
Nitromethane
(CH
3)2CHOH
Isopropanol
3 of
Propanol
H3O+ (CH3CH2)2O
10
((CH3)CH
PO2
2N)33NO
Hexamethylphosphoric
triamide HCON(CH )
CH
3CH2CH2OH
N,N-dimethylformamide
3 2
HCOOH
CH3NO2
Nitromethane
CH3COOH
HO+
BMIM hexafluoro
Water
Ammonia
Ethanol
Water
Methanol
Ethanol
Isopropano
Methanol
Propanol
Isopropanol
Formic acid
Propanol
Acetic acid
Formic
acid
Formamide
Acetic acid
N-methylforma
Formamide
N-methylformam
tert-butyl alco
PCC
OH
Pyridinium chlorochromate
PyH+, CrO3Cl-, CH2Cl2
H
Cl
!C≡CCH2CH2CH3
H
HO
Cl
HO
H
HO
COOH D.
!!
!!
H
!C≡CCH3
H
OH
COOH
E.
A) (A)
4 of 10
=
=
=
=
=
=
=
=
=
=
=
HO
COOH
!C≡CCH2CH3
OH
(CH ) CCl
=
=
= =
=
!
!
!!
!!
=
=
=
=
C.
COOH
!C≡CCH2CH3
H
OH
H
=
=
=
=
=
=
=
=
!
!
=O
=O
!!
!!
=
=
OH
=
=
H3
=
=
=
=
=
=
=
=
=
=
=O
=O
=
=
HO + H!CH !CH
=
=
=
=
=
=O
Cl + (CH ) C
=
=
!
=
=
=
=
=
=
=
=
=
=
O
O
O
O
O
O
Br
CH3CH2CH2CHCH
2CH
2CH
2COH
CH23CH
CH22COH
CH2CHCH
CH
3CH
2CH
2CH2CH
2CH
2CH
2CCl
3CH
2CH2CHCH
2CH
2CH
2CBr
3CH
2CH
2CH2CH
2CH
2CCl
3CH
2CH
2CH2CH2CH2CBr
+ N !HO
O
O
O
O
O
O O
!
Br
NH
CH32CH2CH2CHCH
CH
CH CH CH
2CH
2COH
CH COH
CH CH CH2CH
CH
CH, CH
CrO
2CCl
3CH2CH2CHCH
2CH
2CBr
3CH
2CH2CH2CH
2CCl
3CH
2CH
2CH
32Cl
2Cl
2 2CBr
CH3CH2CH2CH2CH2CH2COCCH2CH2CH2CH2CH2CH33 O2 2 2 23O 2 2 CH
O
O
O
O
CH3
O O
CH3CH2CH2CHCH
CH
CH
CH
COH
2COH
CH
CH
CH
CH
CCl
CH
CH
CH
CH
CBr
3
2
2
2
CH
CH
3
2
2
2 3CH2CH2CH2CCl 3
2
2
2 3CH2CH2CH2CBr
CH3CH2CH
COCCH
Br2CH2CH2CH2CH3
A)2CH2CH2O
O
O
O
O
O
O
O
NaBH
NaBH
4
4, CH3CH2OH
!Br CH CH CH CH COCCH
!Li CH CH=O
CH
HO
CH3CH2CH2COH
CH3CH2CH2CClCH3CH2CH2CCl CH3CH2CH2CBrCH3CH2CH2CBr
3
2
2
2
2
2
2CH
3 3CH2CH2COH
O
O
O
O
O
O
O O
Solvent
light
hν
Δ
Slow
Fast
CH
CH
COH
CH
CH
COH
3
2
CH3CH
3
2
CH3CH(CH
Q)3CH
Provide
the product
+ CH3CH2CCl CH3CH2CCl
2CBr
LiAlH
4 2CBr LiAlH4,
3CH2)2O
CH
2CH2COCCH
2CH2CH3of this reaction:
O
O
O
O
O
O
O O
LDA
OH
CH3COH
CH3COH !
CH3CCl
CHCH
2CH2CH2CH3CBr
CH
+
+ CH
3CBr
3
3CCl
A) CH3CH2COCCH
N Na2Cr
N2O7, H23
3
CH3 2CH3
3 3
SO34, H2O
O O
HN(CH(CH3)2)2
Lithium diisopropylamide
PF6!
O
O
CH3COCCH3
O O
OHOH
+
!
+
H
3CH2)2O
Diethyl ether
HO(CH
2 H 3O
2
2
(CH3)2CH
!Br!Br
!Li !Li
=O =O 2 BMIM hexafluorophosphate
!CH
!CHCOC !CH
!CH
2
2
Acetone
CH3COCH
H+, H2O
O
O(CH3CH2)2Ammonia
Diethyl
Q) Provide the product(s) of this reaction:
+ ether3
NH3
Acetonitrile
Acetone
H
CH3CN
OH
CH3COCHWater
3
H 2O
COC
Ethanol
O O
OHOH Acetonitrile
DMF
CH
CH2OH
HCON(CH3)2
3
CH3CN
Water
CH3CH3
CH3CH3
Methanol
CH OH
! OH
A) 2CH2CH2CH2CH2CH3
CHCH2CH
3 H2C=CHCH
Dimethyl formamide DMF
Ethanol3
C
HCON(CH3)2
r
Br
Isopropanol
H
(CH3)2CHOH
Methanol
DMSO
(CH
3)2SO
Dimethyl
formamide
HCH2CH3 BrCH2CHCH
Propanol
CH
(CH
(CH
)2CH
2CH
2CH
2CH3
3)22CH
3OH
(CH(CH
CH3CH2CH2OH
3)2CH
3)a
2CH
Q)Which
of2CH
the
following
contains
hemiacetal?
O
Isopropanol
Dimethyl sulfoxide
(C
CH
CH
2OH
2CH
3
NaNH
NH
HC≡CCH2CH2CH2CH
CH
2
3
2CH
2
3
CH
OH
DMSO
2
(CH3Formic
)2SO acid
O
HCOOH
HO
O
Propanol
HC≡CCH2CH2C≡CH CH3I
CH3CH2I
HMPA
CH3
3
((CH3)2N)3PO
CH3COOH
OH
Acetic acid
Dimethyl sulfoxide
H H
H H
OH
OH
O
O
Formic acid
CH
CH3CH2CH2CH2I
2I
H 3CH2CHHO
CH=CHCH
2CH3
Hexamethylphosphoric triamide
Formamide
HCONH2
HO
OH
HMPA
HO
((CH3)2N)3PO
Br Br
C
Acetic
acid
OHA. CH3CH2CH2CH2Li, THF H
N-methylformamide
HCONHCH
3
CH3NO2
Nitromethane
! OH
! OH
= O=OH
Hexamethylphosphoric
triamide
Formamide
CHCHCH2CH3
O
H
OH
(CH3)3COH
tert-butyl alcohol
H H
H H
N,N-dimethylformamide
HCON(CH )
N-methylformamide
HC
CH3NO2
Nitromethane 3 2
HC≡CH
HC≡C! B. CH2=CH CH3C=CH2
OH
OH
OH
O O
CH3C≡CH CH3C≡C!
N,N-dimethylformamide
HCON(CH3)2
CH3C=CHCH3
!Li !Li
!Br!Br
OHOH
O O
!C≡CCH2CH2CH3
!C≡CCH3
H O + H C=CH
O
3 2
DMSO
(CH3)2SO
HMPA
OH
Cl
+ NaBH4
H2O
CH3CH2OH
CH3OH
Isopropanol
(CH3)2CHOH
Propanol
CH3CH2CH2OH
Formic acid
((CH3)2N)3PO
HCOOH
OH Acetic acid
Hexamethylphosphoric triamide
CH3NO2
Nitromethane
3
Water
O
Ethanol
workup: CH3CH
Methanol
CH3COCH3
Q) Provide the product
of this reactionCH
after
aqueous
Acetonitrile
3CN
A) CH3CH2OH
DMF
HCON(CH )
3
=
Acetone
OH
HCH
2O + H2C=CH2
CCH
=
HO! + H!CH2!CH2+
Cl
Q) Select the major
product of this reaction:
N,N-dimethylformamide
HCON(CH3)2
CH3COOH
Formamide
HCONH2
N-methylformamide
HCONHCH3
Cl
OH
A.
CH2CN
B.
=
O
O 2N
O2N
CH2COH
OH O
!
!
=
OH
CHCN
CH COH
C.
D.
A) (B)
CH3COCH3
CH3CO
=
=
O
OH
=
=
O
CH3CH2CH2CH2COCH2CH3 CH3CH2CH2CH2COCH3
=
O
CH3CH2CH2CH2CH2CH2COCH2CH3
O
=
=O
=
O
!OH + H+
!OH2+
CH3CH2OH CH3COCH2CH3
3CH
2COCHtoward
3
of these isCH
the
fastest
electrophilic aromatic substitution?
O
CH3CH2CH2CH2CH2CH2COCH3
=
=
=
=
=
CH3COH
O
=
=
=
=
O
=
A)
CH3CH2CBr
O
CH3CBr
H
!
=
=
CH3CH2COH
CH3CH2CCl
H 3C
!OH
O
O4, 130-140°C
H2SO
+
H+
Br! + CH3C—CH
reaction: CH3COH +
CH3CCl
H 3C H
=
O
O
COCH3
CH3CH2CH2CH2CH2CBr
(CH3)3C!OH2+ + Br!
O(CH3)3C+ + H2O
CH3CH2CH2CH2COHH3C H CH3CH
CH3CHH2CH
Br2CH
H 2CH2CCl
H 3C H
H3C
3C 2CH2CBr
(CH3)3C!Br + H2O
O
O
O
+
+
CH3C—COH CH3C—CCH3 CH3C—C—OH + H+ CH3C—CH CH3C—CH
CH3CH2CH2COH
CH3CH2CH2CCl
CH3CH2CH2CBr
O H 3C H
H 3C H
H3C H O H3C H
O H 3C H
Q) Provide the product(s) of this
CH3Q)
CH2Which
CO
=
=
=
=
=
CH3CH2CH2CH2CH2COH
CH3CH2CH2CH2CH2CCl
O
(CH3)3C!OH + H!BrO
O
CH3CH2CH2CH2CH2CH2CBr
O
=
=
=
O
O
CH3CH2CH2CH2CH2CH2COH CH3CH2CH2CH2CH2CH2CCl
O
O
5 of 10
Br
+ + H2O
CH3
NO2
CH2CH3
OH
CH3
CHO
Br
NO2 CH=CH2
H3C
NH2
E
CHO
OH
F2
NO
A.
C
COOH
Br
NO32 OHC
CCl
COOH
CH3
OH
CH22CH
Cl Br
CBr
NO2 3
CH
23F 2NO2 OHC
CH
CHCl
COOH NH2
CH3
OH
=O
CHCl2 F3C
SO
CCl
3H 3
2CH
NO2
CHF
Cl
CCl23 CH3
C.
COOH
CHO
OH H2N
CF
Br3
B.
NH2
H3CC
CF3
COOH
CH2CHCH3
OH H2N
CHF2
COOH
D.
CF2CH3 F3C
CH2ClCF3
E.
A) (A)
CH2F
F3C
=O
SO3Na
CH3
H3CC
CH3
CH2CHCH3
=
=
=
=
=
!
! !
=
=O
!
=
!
=O
=O
=
OH
A.
3. Zn(Hg), HCl
OH
OCH3
=
=
!
!
!
=
=
!
=
=
!
==
=
!
=
=
!
!
=
=
=
=
=
=
=
!
=
!
=
!
=
!
!
3. Zn(Hg), HCl
=O
! =O
=
= !! !!
! ! != !
=O
==O =!
== = ! =
=
=O
!=
!
!
=
==
=
=
! !
=! !
!=
=
!=
=O
=
=
!
=
=O
=O
! !
!
! ! !!
=
=
OH
=O
! !
=O
H 3C H
Br H
H 3C H
H 3C
H3C
O
O
O
O =O
+
+
CH3C—COH CH3C—CCH3 CH3C—C—OH + H+ CH3C—CH CH3C—CH
CHO
CCH2CH2CH3
HCCH2CH2CH2CH3 HCCH2CH2CH2CH2CH3
CH3CCH2CH2CH2CH3 CH3CH2CCH2C
H 3C H
H 3C H
H 3C H
H 3C H
H3C H
O
=
O
O
H 3C
CH3 O
=O CH3CCH2CH2CH
OHNH
O2CH
2CH
CN
CHO
N=C(CH
+
3) 2
Pyridinium
chlorochromate
+
!
NH
NH
HPCC
Br + CH3C—CH
CH3=
!OC ! CCH3
Q) Provide the product(s) of this reaction: CH3 CHC≡CCH
+
NaCN
CH
3
3 CC≡CCH3
HCH
CH3CCH3 CH3CH
HC=OPyH+, CrO3Cl-, CH2ClO2
H23C H Base
CH=CH
OH
SbClO
BF3
H2, Pd
O
FeBr3CH3FeCl3
AlBr3
AlCl
5
3OH Acid
C≡N
C≡N
C≡N
HO
CH3
O
H23 CHC≡CCH3
CH3 CC≡CCH3
H
,
Ni
CH3 CC≡CCH
2 3 CHC≡CCH
2CH3
2CH3
O
H2SO4, 100°C HF 0°C CH
O
CH3 O
OH
OH
CH3
CH3CCH
3 CH3
O
CH3 !OCO! O ! CCH3
OH
O O
OH
O
A) OH
CH
CH
OH
CH
CH
COCH
CH
3
2
3COH
3
CH3CH2CuLi CH3+CH
N2CH
!H 2CuLi2 3
C ! CCH3
CH
CH3CH2CH2CH
2=CHCH
CH
3CH2CHCH
CH
H3 CHC≡CCH
CH
HO
C≡N
3
2CH3
3 CC≡CCH23CH3
CH
CHC≡C(CH
)
CH
CH
CC≡C(CH
)
CH33, H2SO4
CH
CH
CC≡CCH
3
2
2
3
3
2
2
3 CHC≡CCH
33
HCH3
HCCH2CH3 CH3CCH3
Zeolite, 140°C !HNO
HCCH
CH
CrO
Cl
,
CH2Cl2
3
3
OH
CH
O
O
3
OH
CH
CH
CH
CH
O
CH
CuLi
CH
CH
CH
CH
CuLi
OH
3
2
3
3
3
2
2
2
OO
CHFe,
3 HCl
Zn(Hg), HCl
SO3, H2SO4O
CrO3, H2SO4, acetone, 0°C
CH
O
3
H3 CHC≡C(CH2)2CHQ)
CH
CC≡C(CH
)2CH
!C
C!O
! CH
3 CH
3
3CH
CH3 CHC≡C(CH
Provide
the3CH
of! this
reaction:
CH
2)3CH3 CH
3 CC≡C(CH2)3CH3
OHOH
3 3CHC≡CCH
22product(s)
3 CH
3 CC≡CCH
2CH
3 3
Br
CH
2CH2CH2CH
CH
C
!
O
!
CCH
OH
3CH2CH2CHCH
O
3
OH
O
TMEDA
CH
3
CH3
H2CC≡N
O
NO
NO
2CH
NaBH4 O
NaBH4, CH3CH2OH
H3 CHC≡C(CH
CH3PBr
CC≡C(CH
CH3OCrO
CH
2)3CHA)
3 CH
3CHC≡C(CH
22))32CH
33 CH
3
!
AlCl
CH
CC≡C(CH
)2CH
3CCl,
3 2 HO
3COOH
3, H2SO4, H2O
3O
2CF
3
3
CH
3CH2CH2CH2CH2CH
CH
CH
CH
CH
CHCH
CH3 O
3
2
2
2
OH
CH3CH2O
COCH3
CH3C=CHCH2CH3
H3C CH3
C ! C ! O ! CH3
O
O
!
CH3 CHC≡C(CH2)3CH3 CH
CC≡C(CH
)
CH
2 3
3 COH O
LiAlH
LiAlH4, (CH3CH2)2O
COHCH
4 3
O2NH
COH
O
O3
HHOCH2CHCHCH2Br
H
OH
CH3 1. Br2, Br
FeBr3 Q) Provide
1.
Br
,
FeBr
1.
H
SO
,
HNO
H
Br
HCH
CH
CH
2
3
2
4
3
CH
CH
C=CHCH
the enolate
that arises
3
32CH22CHCH
3 of
CH3CHCH
CH2CHdeprotonation
CHion
2from
3CH2CH2CH2CH2H
2CH
CH2Cl
H
HCH
3C CH
!
! 3
!
!
O2.
2. CH
Br2, FeBr3 3
O
3CHO
2Br, AlCl3 O 2. HO
2SO4, HNO3
O
Na2Cr2O7, H2SO4, H2O
NO2 CH3
NO2
CH3
CH3
CH3
Br22CHCHCH
CH23CH3 HC=CHCHBr
BrCH
2Br
CHCH3 CH3C=CH
=CH HC=CHCH
CH
A)
2CH
2
3
2 CH
O
O
CH3CCH3
Br
H
H
3
O
+
1. CH3COCl,CH
AlCl
1.
Br
,
FeBr
3
2
3
H
H 3O
O
O
HOO
O2N H
CH3
CH
CH
H
Cl
H
3
3
O2CuLi CH
O
CH32CuLi
2. Br2Cl
, FeBr3
2. CH3COCl, AlCl
1. Br2, HBrCH3CH
O
3CH22CH
3
H
Cl
HCCH
CH2=CHCHH CH3CH2CH2CH H
+, 3H
CH3CH2CuLi CH3CH2CH2Cu
CH3CH2CHCHCH3
CH3CH
CH2CH
LiO CHH
CH
CH
2O2CH2Li
O
2.
HNO
3. Zn(Hg), HCl
3.
Zn(Hg),
HCl
CH
=CHCH
CH
3
2
3
2
2
CH
CH
CHCH
Q) Provide the product of this reaction:
3
2
CH3
CH
CH
3
3
CH
CH
CH3CuLi OCH3CH2CH2CH2CuLi
3
NO3 2
NO
22 Cl
O CH
Cl
3CCH
2CH
3
CH CH2
CH3CuLi CH3CH2CH2CH2
CH=CHCH2OCH3
CHCH
CH
3Li
3CH2CH2CH2Li3
O
O
1. SO3, H2SO
4
O
CHA)
H 1. HNO3
O
3 CH3CH2CH2CH
CH
1.Cl2Br
2, HNO3
CH3CH2CH2CH2CH
CH3CH2CH2CHCH
2. HNO3, H2SO4
2. HO2, Pd COOH
2. FeBr3 COOH O2H
CH3CH2CH2CHCH
N HCCH2CH2CH3COOH
Br
Br
Br
CH3 Br
3. Zn(Hg),
HCl
OO
O
O
CH3
CH
2CH2CH
2CHsynthesis for the reaction below:
Q)3CH
Select
the2CH
best
CH
3CH
2CH
2CH
2CHCH
CH
CH
CH
CH
3CH
2CH
2CCH
2CH
2
CH3CH2CH2CH2CHCH
3
2CH2CH3
OH 1. NaOH, NH
OCH
1. NaNH2
1. H2SO
OH3
OCH3
4 3
O CH3
O
O
CH3
SO3HNH3
2. SO3, H2SO4
2. H2SOO4 2N
2. NaOH,
O
O
CH3CH2CCH2CH3
CH3CH2CH2CH2CH2CHCH
CH3CH2CH2CH→
2CH2CH2CH
CH3CH2CH2CH2CH2CHCH
CH3CH2CH2CH2CH2CH2CH
O
CH3
1. SO3, H2SO4
1. HNO3, H2SO4
CH3
Cl
Cl
Cl
Cl
2. HNO3, H2SO4
2. SO3, H2SO4
CH3COOH
OCH3
CH3CH2Li
CH3Li
CHCl3
CH
2Cl
2 2CH2Li
CH
3CH
CHCl3
CH3CH2CH2CH2Li
6 of 10
SO,4FeBr
2. NaOH, NH3
1. H
CH
Br, AlCl3 2. SO
1. CH
AlCl32. H2SO
1.
, FeBr
3, H32COCl,
3CH
3
1.2SO
Br42, 2FeBr
1. Br
1.4Br
H22SO
1. CH3CH2Br, AlCl3 2.
3
2
3
4, HNO3
2.
Br
2.
Br
2.
CH
1. Br2, HBr
2, FeBr3
2, FeBr3
3COCl, AlCl3
2. CH3CH2Br, AlCl3
2. H2SO4, HNO3
2. Br2, FeBr3
2. Br2, FeBr3
2. HNO3
3. HNO
Zn(Hg),
3. Zn(Hg),
3.3,Zn(Hg),
1.
1. SO
1. HNO
H2SO4 HCl
3, HHCl
2SO4
3, H2SO4HCl
2. Zn(Hg), HCl
2. HNO3, H2SO4
2. SO3, H2SO4
1. CH3CH2Br, AlCl3 3.
1. 3CH
COCl,
AlCl3.
1. 3Br
FeBr
3 Zn(Hg),
1. SO
HNO
1. SO
, HCl
H2,2SO
,H
SO
3, 23H
2SO
4 3 3. Zn(Hg),
4 4
1.HCl
Br , HNO
1. HNO3
2. Br2, FeBr3
2.3Br
FeBr
2. CH
COCl, AlCl3
1. Br22, HBr 3
2. SO
, H22, SO
2. HNO
4 3
3, 3H2SO4
2. H2, Pd
2. FeBr3
2. HNO3
3. Zn(Hg), HCl
3. Zn(Hg),
HCl
3. Zn(Hg),
3. HNO
Zn(Hg),
3. Zn(Hg),
HClHCl
1.
3, HHCl
2SO4
2. Zn(Hg),
1. Br2, FeBr3
1. BrHCl
1. H2SO4, HNO3
2, FeBr3
1. 2.
HNO
H2SO
1. ,SO
4
3, H2SO4
1.
NaNH
1.
NaNH
2
2 Br
3
1.2Br
1. HNO
2, HNO
3 1. H2SO4
3.
SO
H
SO
CH33,CH
Br,
AlCl
2.
H
SO
,
HNO
2.
, FeBr
3
2 2 4 4
2
3
3
3 1.3 NaOH, NH
2. SO3, H2SO4
2.
HNO
3, H2SO4 2. SO3, H2SO
2.
H
SO
2.
H
SO
2. NaOH, NH3
2
4
4
2
4
2.
H
,
Pd
2.
FeBr
2
3
4. CF3CO3H
3. Zn(Hg), HCl B.
3. Zn(Hg), HCl
1. CH3COCl, AlCl31. HNO1., Br
2, FeBr3
1. SO3, H2SO4
3 H2SO4
Br2,2FeBr3
2.
CH
1. Br
3COCl, AlCl
3
1. 2.
NaNH
1.
NaNH
1. HNO
NaOH,
NH
2
3 42, HBr1. H2SO4
2. Zn(Hg), HCl
2.
3, H2SO
2.
HNO
HCl 3.
Zn(Hg),
HCl
2. 3.
H2Zn(Hg),
SO4
2. SO
SO33,,3.
H
SO
2.
H
SO
2
4
2
4
3
O
H2SO4
3. Zn(Hg), HCl 3 2. NaOH, NHO
O
O
=
C.
OH
HOCH2CH2CH2CH2CH2COH
=
O
1. SO3,3,HH
2SO
1. HNO
1. SO3, H21.
SOBr
2SO
44
4 2, HNO3
1. HNO3
HOCH
CH
CH
CH
CH
2. HNOHCl
2
2
2
2
2COH
3, H2SO4 2. HNO3, H
2. Zn(Hg),
SO
2.2H
2. FeBr
2,4Pd
3
3. 3Zn(Hg),
3. SO
, H2SO4 HCl 3. Zn(Hg), HCl
O
D.
1. H2SO4
2. NaOH, NH3
O
O
=
1. NaOH, NH3
2. H2SO4
CH3 HO HO
H
H3C
OH
=
O
HOCH
O 2CH2CH2COH
OH
O
H
H
H
OH CH3
HOCH2CH2CH2COH
OH
O
CH3
C=CHOCH2CH
Br C
Br
A)
OH CH3CH2
Q) Provide the product(s) of this reaction: CH3CH2C≡CCH2CH3
H2O, H+, HgSO4
CH3
=
O
OH
CH3CHC≡CCH2CH3
=
=
=
O
O
=
=
(c)
CH3
O
O
O
=
CH2CH
O
=
CH3
O
=
O
=
=
O
=
CH2CH2CH
CH3
O
=
O
CH3
=
=
=
CH3
O
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
+ CH2=CHCCH3
CH2CH2CCH3
O
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
CH3
CH2CH2CCH3
=
=
=
O
=
Q) Provide the product of this reaction:
=
=
=
=
O
=
OCH3CH2OK, CH2CH
O2OH, (CH3CH2)2O
O
CH2CHO
2CCH3
CH2CH
CH2CCH3
CH3
O
O
CH3
CH3 O
CH3
O
CH2CH
CH2CCH3
CH3
= =
O
O
O
=
=
A.
B.
C.
D.
E.
A) (E)
O
=
(b)
Fastest to slowest
a>b>c
b>a>c
c>a>b
a>c>b
b>c >a
O
O
=
(a)
CH3
7 of 10
C
Br
CH
O
CH3CH2C=CHCH2CH3 CH3CH=C
H
Q) Rank these compounds in the order of decreasing reactivity toward electrophilic aromatic
substitution.
O
C=C
HOCH
O
CH3CCH2CH2CH2CH
A)3 CH3CH2CCH2CH2CH3
C=C
CH3
CH3
OH
H
CH3
H
H2SO4, H2O
=
Q) Provide the product(s) of this reaction:
H
HO
HOCH2CH
E.
O 2CH2CH2COH
A) (B, Sulfonation conditionsHOCH
in step
32CH
are2CH
milder)
2CH
2COH
=
1. NaNH2
2. SO3, H2SO4
O
Os
=
O
=
O
= =
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
=
CH2CH2CCH3
O
CH3
CH2=CHCCH
HO3
CH2CH2CH3
→
O
O
CH3
H3
CH2CH2CH2CH
O
=
O
=O
=
CH3
CH2CH
A)3
=
=
CH2CH
CH2CCH3
CH3CH2OK, CH2CH2OH, (CH3CH2)2O
CH3
CH3
CH2CH2CCH3
O
O
O
=
CH3 O
O
O
O
=
=
O
CH3
COCH2CH3
=O
HO
(CH3)3CO
O
OH
=O
H2SO4
(CH3)3CO
CH3
O
=
O
CH2CH2CH
CH3
=
3
CH2CH
CH3
O
O (CH3)3CO
NaOH
OH
O
O
H2SO4
!CH3
CH3
NaOH
H
Q) Provide the product of this reaction run at lowBrtemperatures
(5°C):
O
2, P (trace)
CH3CH2CH2CH2CH2CH2CNHCH3
OH
COCH
CH
OCH3 O2N CH
OCH
2
3
3
OH
CH
CN
NaBH
O
N
CH
COH
2
2
4, NaOH, H2O
2
2
O
O
O
CH3
O
OH
OH
OH
OH
O
CH
CHCH
Br
CH
CHCH
Cl
3
3
3
3
CH3
O 2CNHCH3 (CH
CH
CH2CH2CH
H 3CH2O
3)3CO
!CH
Hg(C
2H3 O2)2
CH3OCH
CH3O
C(CH3)2 CH3CHCH3 CH3CHCH2CH3
A)
O
OH2C(CH
OH
H 3)2
HCH CH3CH
CH3
HgC
2H3O2
BH3, THF
CH3
2CH2CH2CNHCHCH
3
CHCN
CH COH
O CH3CHO
!CH3
3!
O
OH
OH
THF
COH
CH
OH
H2OH
O2, NaOH, H2O
O
r
3
OH
OH
Q) Provide
theOproduct(s)
of thisOCH
reaction:
CH3C≡CH
+ (C26HCH
11)32BH
CH3CCHCH
3 3CH2CH2CH2CH2CH2CNHCH3
CH3
OH
CH
OH
3CH2CH2CNHCH3
H
O
CH3OCH2C(CH3CH
)2 2OH
CH
CH3CHCH3
3C(CH
3)2
O
HgC
2H3O
2
O
CH3 CH3
H
A) HCCHCH
2CH
3
Cl!
H
!CH
OH
CH
3CH2CH
Br!
CNHCH
!CH3 3
3CH2
3 2CH2CH2CNHCH
Br O3
CH3
O
O OH
OH
(CH3)3CO
O
D
CH3CH2CH2CH2CH2CHCOH
O
CH3
CH3CCH2CH
CH33CNHCH
CH3
CH3CH
3 2CH
Cl
Br2CH2CNHCH
O 3
CH3 BrOO
O
O
O
O
COH
O
CHCH
3 2OH
OH
CH
3
CH
CH
CH
CH
CHCOH
3
2
2
2
H
CH3CH2CH2CH2CH2CH2COH CHHBr
CH3CH2CH2CH
(trace)
3CH
2CH2CH2CH2CCl
2CH2CH2CBr
2, P2CH
OH
CH
CH
HO!
3CH
2O
2CH
2CH2CH
2CNHCH
3 !CH
Br!CH
2CH
2CH
3 product(s)
OCHHO
3
Q)HCCH
Provide
the
reaction:
HO!
CH
CHthis
3CH2of
2CNHCH
3 3H
OO 3
Br
O
O
H
CH
OH
2
O
(CH3)3CO
O
D
CH3
O
CH
3CH2CH2CHCOH
CH3CH2CH2CH2CH2CH2CNHCH3
Pyridinium
chlorochromate
CH3CH2CH2CH2CH2COH
CH3CH2CH2CH2CH2CCl PCC
CH3CH2CH
2CH
CH
3 2CH2CBr
CH
CH
3O
2COH
3 3
CH3 CH3BrOO
CH3CCHCH
2CH
2CH
3 2CH2CH2CNHCH
CH3CHCH
2CNHCH
3O
O
O
OCH3
CH
3
O
+, CrO Cl-, CH Cl
O
O
PyH
3
2OH
2
CH
CH
CHCOH
3
2
CH3CH2CH2CH2CH2CNHCH
CH3CH2CH2CH2COH
CH3CH2CH
CH3CH2CH2CH2CBr
2CH
OCH
Br 3
3 2CCl
Br
NH
H CH3CNHCH
Br
Br32
H Br O
3CH2CH2CH2CNHCH
3
HO
A)3CH2CCHO2CH
CH
CHCHO
3
O
O
H O
CH3
COH
CH2OH
O
3CHCOH
CH3O
H H CH3CHCH
OCH
CH3CH2CHO2CH2CNHCH3
2CH23COH
CH
CH
CH
CCl
CH
CH
CH
CBr
3
2
2
3
2
2
O
CH2CH2CNHCH3
+ N !H! :
Cl
O
O
O CH3OH
NO2
COOH BrCHOCOH
O
Solvent
2
light
CH3COOH
hν
Δ
Slow
Fast
CH
CH
CH
2CH3
2
3
!
CH
Q)3CH
Provide
the product(s)
of this reaction: CH3CH2COH + CH3NH2 CH3CH2CCl
CrO3Cl , CH2Cl
CH
2 3CH2CBr
2CH2CNHCH
3
CH3CH2CNHCH3
O
CHCl3 O
O
O
Br O
CH3
!
OCH3
O NH2
LDA
CHO
CH
Cl
CH
COH
CH
CH
CH
CH
2
2
2
2
2 CH33CBr
3 2CH2CH2CHCOH
CH
+
CH
3
3CCl
CH
CH
CH
3
2
CH
CH
CNHCH
3
2
3
A)
N
N
CH3CNHCH3 Lithium diisopropylamide
CHCl3 O
)2 CHN! RC!
HOCHN(CH(CH
! Br
ROOC!3)2R
PF6! NaBH , CH CH OH
NaBH4
4
3
2
CH3CHHO
2CH2CH2CHCOH
CH
CNHCH
3
3
lCC2HC3HC lCC3HC
NO2
OH Br
COOH
NO
Br
O
2
Br
NO
2
(CH3CH2)2O
Diethyl ether
BMIM hexafluorophosphate
CH3CH2CH2CHCOH
LiAlH4
LiAlH4, (CH3CH2)2O 3
Acetone
CH3COCH
lCC2HC2HCAmmonia
3HC 3HCCOC3HC lCCH
Br O3
NH3
Q) Provide
OCH3
Br
NH2 Brthe IUPAC name
OH of this compound:
NHCCH3
Acetonitrile
CH3H
CH
CH23CHCOH
CN
Water
A)2 OHC
cyclopentanecarboxylic
NO
OH H2acid
N
COOH
: !
Br O
Na2Cr2O7, H2SO4, H2O H2O
Ethanol
DMF
CHH
HCON(CH
)
3CH
2OH
3
2
H
OC
H
O
CH
O 3CHCOH
Br
Br
O!
H
Methanol
CH3
CH3OH
H
H 3O +
Dimethyl
H formamide
HO
BrCH
2COH
OCH
3
Isopropanol
(CH3)2CHOH 3FC
H3CCOCH3
CH2CHCH3
CF3
F3C NHCCH3 O2N CH3
O2N
DMSO
) SO O3
H+, H2O
FeBr3 (CH
FeCl
AlCl3
CCl 1)CH
CCl
3CH22)
Q) Provide the product(s) of this reaction:
+3 23CH3AlBr
Propanol
CH3CH2CH2OH
H3C Dimethyl sulfoxide
Acid
OCCF
3
Formic
acid
HCOOH
SO3H
3
HCCl CH3COCCH3
HMPA
CH3C
OCH3
((CH
3)2N)3PO
CH COOH
Base
Acetic acid
=
!
=
=
=
=
=
=
=
!
=
=
O=
=
! !
== =
O=
O=
O=
O=
=O
= :=
=
=
!
=
=
=
=O
=
=
=
=
=
=
=
=O
! ! ! !
== == == == ==
=
=
=
=O
=
=
O=
O=
O=
O=
O=
=
=O
O=
=
OH
!
=
=
=
=
!
!
=
!
=
!
!
=
!
=
=O
=
=
=
=
=
H
=O
3
Hexamethylphosphoric CH
triamide
CH3NO2
OCCF3
N,N-dimethylformamide
HCON(CH3)2
Nitromethane
(CH)3C
CH3
C(CH3)3
8 of 10
=O
=O
=O
=O
=O
=O
=
=O
=
=O
O=
=O
:
CH3
A)
3
Formamide
HCONH2
N-methylformamide
HCONHCH3
tert-butyl alcohol
(CH3)3COH
)2$3-,4$&'$%/05$#$,*#01&-'$&3$*&15*,
O
OH
4+-/'.%$.-*%$'-1$0-'1#&'$#'$D
52.,-(*'
HO
H2SO4
(CH3)3CO
H
CH3
Q)Provide the product of this reaction:
NaOH
+
,
!
&'!$"($"#
O
%))"(!
"#$
(CH3)3CO
$"#$"(!"
H
A)
/6,
78
H 3C
H
O Br H
H 3C
H
H 3C
H 3C H
H 3C
H3C
+
+
!CH3
CH3C—COH CH3C—CCH3 CH3C—C—OH + H+ CH3C—CH CH3C—CH
H
H 3C
<=>
CH
3
H
=
=
H 3C
OH
OH
O OH O
H
+
! + CH3C—CH
H
Br
H
H+
Br
CH3OCHof
CH3C(CH
CH
2C(CH
3)2reaction: HCH
3)22CH
H
Br
CH
Q)
Provide
the
product
this
+
NH
3CH
3 3CHCH3
H
H CH3
CH3
H 3C H
O
O
O CH2=NCH3
O
A)
CH
CH
3
Br
CH3 O3
Br
OH
CHO
H2CH2CH3
CH3CCH2CH2CH2CH3 CH3CH2CCH2CH2CH3
3CCH3
(CH3O
)2S
CH3
Br
H
H CH3O
OH
O
O
O
CH
CH
OH
CH
CH3COCH2CH3
3
2
3COH
O
O
O
O
O
H
Cl
H
H (CH3)2S
CH3
H
Cl
HCCH2CHO3 3, CH2Cl2 Zn, HC2H3O2
Q)2CH
Provide
of2CH
this reaction:
OH
CH2CH
CH
HCCHO
CH32CH
H
2O
2CH
H 2CH the product(s)
O H HCCH2CH
OH
O
H O
O
O
O
Zn,
HC2H3O2 (CH3)3CO
D
CH
CH
3
3
O
O
O
Cl
CH3
Cl
CH3CCH
CH3
OH2CH3
Br
HCCH2CH
HCCH2CH2CH
A)
Os
OH!, H2O
O
O H CHCH
CH3
Cl
3
CrO3, H2SO4, H2O
2OH
O
OCH3
COOH OH
H
OH
O
O
HCCH2CH2CH3
H3
Br
Br Os
Br
HO
(CH3CH2)2O
PCC,CH2Cl2
H H of thisCH
3CH2MgBr,
O CH
H
Q) Provide
reaction:
3CH2CH2OH
H
CH3
O theOproduct(s) OH
HO
HO
CH23
OH
Cl 3CH2CHO NO
OHC
CH3CCH2CH
2CH3
HO
A)
CH
OH
OCH
H
3
OH
OCH3
O
H3C H
HO
HO
HO
CH
O
=
=
3
CH3 HO
H
CH
CH
CH
NH
3
2CH3
NH
OH
2ring is deactivated relative
!Li 22CCHto
H3C
benzene?
CH3
H Q) Which benzene
H CH3
(CH
CH
)
O
3
2
2O
H
OH
Cl
Cl 3 OH
Cl
CH
COOH
NO2 OHC
H3C
OH CH3COOH
$&%$%&('&3&0#'1)2$4-,*$#0&.&0$15#'$15*$-15*,O
CHCl
3
OH OH
OCH3
OH
OCH3
A.
OHCOH
OH
NH
22
CH
2Cl
NH2
!
!
CHCl3
OH
H
OH
OH
HOOC
#
OH
&'!$"($"# H3C
OH !$"($"
COOH
CH3
$"($"#
B.
$"#$"(!"
%))"(!
,-'-,
OH
C.
NH2
NH2 Br
CH3O
=?>
OHC
CH3 OH
COOH CH3O
OH
D.
CH3 CH2CH=CH2
NHCH
2 3
CHCH3
CCH3
OHE. CH3O
CH3
CH3
NH2
A) (C)
=O
CH2CH=CH2
Br
CH2CH=CH2
CH3O
CCH2CH3
,1A0'7 B0620 C,'1-D24E
-/'.%<$65*'$1,*#1*.$6&15$:#%*<$0#'$/'.*,(*#01&-'<$(&=&'($#$020)&0$+,-./01
CHO
MgBr
MgCl
9 of 10
H 3C
H
H3C
H
SO3H
CH2CH2CH2CH3
Cl
CH2CH3
OCH3
=O
Cl
=O
=O
CrO3, H2SO4, ac
=O
=O
Fe, HCl
CCH3
CCH3
==OO
==OO
Cl
==OO
Cl
=O
HO3S
Q) Provide the product
of this reaction:OCH
2 3
CH2CH3
O
CH3
O
FeBr3
CHH
2CH2CH3
AlCl3
OHH , Ni
2
HF 0°C
Solvent
=
CH3
Base
SbCl5
O
BF3
H2, Pd
H2SO4
CH3
Fast CH
HCCH
2
3
HCCH3
Q) Predict the product of thisHCH
reaction:
O
Acid
AlBr3
H2SO4, 100°C
(CH3)3CO
HO
CH2CH3
FeCl3
=O
Cl
=O
CH3
=O
A)
=O
=
OCHO3
=
OCH3
==OO
OCH3
=O
Zeolite, 140°C
=O
OCH3 CH3CH2
CH2CH
CH2CH2CH3
A)3
SO3, H2SO4
CH3CCH3
CH3CCl, AlCl3 CF3COOH CrO3, H2SO4, H2O MnO2, CH3Cl, 2
Cl
!, triethylene glycol, Δ
NH
O,CH
OH
CH
CH
CH
CH
2CH
2CH
3 3 2NH2, H2CH
2CH
2CH
2CH
2CH
3 3
2CH
2CH
2CH
2CH
2CH
2CH
3 3
H3CC
OCH3
CH
3 3
reaction: CH
=O
Q) Provide the product of this
O
NaOH
Slow
CH
3
1) 3CCH
hν
Δ
140°C
2)Zeolite,
light
HNO3, H2SO4
chlorochromate
PCC 0°CPyridinium
CrO3, H2SO4, acetone,
Cu,CH
air, 21atm
CH2CH2CH3
CH3
+
N
N
-, CH
Lithium diisopropylamide
3 2 2
(CH3)3CO
!CH3
! 2Cl2
PyH+, CrO3ClPF
6
H
A)
CH2CH2CH2CH
CH3CCl, AlCl3 CF3COOH CrO3, H2SO4, H2O MnO2, CH3Cl, 25°C
3
CH2CH2CH3
(CH3CH2)2O
Diethyl ether
!, triethylene glycol, Δ
BMIM hexafluorophosphate
O
NH2NH2, H2O,
OH
O
CH
O3
Acetone
!H
Acid+ NBase
SbCl5
BF3
FeBr3OH
FeCl
AlBr3
AlCl3
3
OH
OH
CH
3COCH3 O
O
O
CH2CH3
CH2CH2CH3
Ammonia
O
O 2C(CH3)2
3
, Ni3
HF 0°C H2CH
O
CrO3Cl!, CH2Cl2 NH3
100°C
2SO
4,CH
CH3OCH
CH3C(CH3)2 HCH
3CHCH
Acetonitrile
CH
333CN
(CH
(CH
CH
CH33CH
CH22)Br
CH
2CuLi CH
3CH
2CH
2)2CuLi
Water
2CH
2Br
CH
3
H 2O
3
CH2=CHCH CH3CH2CH2CH
CH3CHN!H
2CHCH
Ethanol
+
DMF
CH
CH2OH
HCON(CH
)
3
3 2
H
CH2CH2CH2CH3
CH
OH
(CH
CuLi CH
(CH
3CH2
2HCH
3CH
23CH
2CH
CH33)Br
CH
HCCH
CH3CCH3
Zeolite, 140°C
HNO3,
CH2CHO
3HCCH
2CH
2CH
2Br2)2CuLi
2CH3
2CH2CH3
O
Q) Provide the product of this reaction:
CH CH
CH2CH2Methanol
CH3
CH3OH
O
Dimethyl
formamide 2 3
CH
3
NaBH4
NaBH4, CH3CH2OH
O CH3CH2CH2CH2CH
HO
Zn(Hg), HCl
SO3, H2SO4
Fe, HCl
CrO3, H2SO
O
4, acetone, 0°C
Isopropanol
CHO
(CH
3CH2CH2CHCH
O
3)2CHOH
CH2CH2CH3
CH2CH
2CH3
DMSO
CH
CH2CH
3
(CH3)2SO
3
O
CH
CH
O OH 2 3 Propanol
H
CH3
CH3CH2CH2OH
LiAlH4
LiAlH4, (CH
H2CH2CH2CH
3CH2)2O
CH3CH2CH
Dimethyl
(CH3sulfoxide
)3CO
CH3CH2CH2CH2CHCH
D
Formic
acid
CH3CCl, AlCl3 CF3COOH CrO3, H2SO4, H2O MnO2, CH3Cl,
25°C
HCOOH
HMPA
CH3 CH3
((CH3)2N)3PO
CH3
CH
A)
O3
CH
CH
O2CHH
CH3COOH
O 23CH2CH2CH3 CH3CH=CHCH
2CH2CH3
Acetic
!, triethylene
2CH3 NH
CHCH
H2C=CHCH
2CH
Na
2C=CHCH
2CH
2CH
2CH2CH
3 2CH
OH
Δ32Cracid
2O7, H2SO4, H2O
2NH2, H2O,
OH 2 glycol,
Br
Br
Br
CH3O
CH2CH
Hexamethylphosphoric
triamide O
Formamide
CH3CH2CH2CHCH
2CH2CH2CHCH
2CH2CH2CH
HCONH2
O
3CH=CHCH2CH2CH3
HO O
O
O
CH
OHH
CH
CH
N-methylformamide
3
HCONHCH
2
3
3
CHCHCH2CH3 BrCH2CHCH
CH
2CH
2CH
+3
3 CH
CH2CH
NO2CH
2CH
2CH
3 H
2
H2CH
CH3CH2CH=CHCH2CH3 CH3Nitromethane
3O
N!H 3
HO
CH
C≡CCH
CH
2 =O3
HC≡CCH2CH2CH
CH CH CH NaNH2 NH
3
O 3
(CH3)3COH
alcohol
H+ 2 2 2 3 tert-butyl
H2C=CHCH2CH2CH=CH2 N,N-dimethylformamide
HCON(CH
3)2 CH3I
H3+CH
, H22O
HC≡CCH
O
2CH2C≡CH
CH
I
CH
3
BrBr of thisBrreaction:
Q) Provide the product
1)
2)
3)
CHCH
2CH2CH2CH3
CH
2CH2CH2CH3
CH
3CH2Li CH3CH
3CH
2CH
2Li3CH
CH
I
CH
CH
2
2
2
2CH2I
BrCH2OH
CHCH2CH2CHCH2Br CH3CHCH=CHCH2CH3
Br
Br
H
C
O
O
O
3
CH3
CH2CH2CH2OH CH2CH3
CH
3Li 2CH3 CH3CH2CH2CH
CH
CH2Li
2CH
2CH2CH2CH3
CH3CHCHCHCH2CH3
CH3CHCH≡CHCH2CH3
LDA
SO3, H2SO4O
=O
Zn(Hg), HCl
O
=O
CH2CH3
Fe, HCl
OH
HN(CH(CH ) )
=
=
=
! =O =
=
= =
=
A)
!C≡CH
!
CH!C≡C
3
!C≡CH
!C≡C!
!C≡CH
!C≡C!
HC≡CH
HC≡C!
CH
3
!
CH3C≡CH CH
3C≡C
!C≡CCH3
!C≡CCH2CH3
!C≡CCH2CH2CH3
!C≡CH
!C≡C!
10 of 10
CH3
!C≡CCH2CH2CH3
!C≡CCH2CH3
!C≡CCH3
=O
=O
=O
=
=
=O
!
=
=
=
=
=
=
=
=
=
!=
=
=
!
=O
=
=
=
=
=O
=
=
=O
SO3H
HCCH2CH3
HCCH3
Zn(Hg), HCl
3
O
=O
=O
HCH