O

Cl
1.
2.
3.
4
5.
6.
O
OCH(CH
3
)
2
HOCH(CH
3
)
2
? =
O
O
? =
H
3
O
+
!
O
OH
OH
O Cl
O
1 mol equiv. NaNH
2
O NH
2
O
OH
O
Cl
O
O
O
SOCl
2
NaOCH
3
O
O
O
NaOCH
3
1.
2. H
+
OH
O
O
OCH
3
Br
NaCN H
3
O
+
!
O
OCH
2
CH
3
HOCH
2
CH
3
H
+
? =
? = ? =
? =
Organic Chemistry 2 - Exam 2 - Worksheet
SI Leaueis: }ustus Philip & Evan Albazi
Fall 2uu9 - CBN 222u




7.
8.
9.
10.
11.
12.
Preform a soaponification reaction with the following ester and name the product:
(H
3
C)
2
CHC(H
2
C)
4
OCH
2
CH
3
O
? =
? =
(H
3
C)
2
CHC(H
2
C)
4
OH
O
7-methyloct-6-enoic acid
KOH, H
2
O
Is this reaction possible? Explain why or why not.
Cl
O
NaF
F
O
NaCl
+
Br
NaCN
CH
3
MgBr H
3
O
+
!
O
H
2
N OH
O
SOCl
2
NH
O
N
O
H
3
O
+
!
NH
O
OH
O
O
NaO 1.
2. H
+
O
O
? =
? =
? =
Yes the reaction is possible. This is because the
better leaving group (weaker base) is leaving.







13.
14.
15.
16.
17.
18.
OH
O
CH
3
MgBr
O
OMgBr
O
+ CH
4
Remember, acid plus base = salt!
This is a no reaction, it just makes
explosive methane!
O
O
HOCH
2
CH
2
CH
3
H
+
O
O
OH
+
HO
O
O
H
O
O
O +
H OH
O
Cl Cl
O O
NaO
H
+
ONa
O
O
O
O
+ NaCl
O
NH
NaOCH
3
No Rxn
O
O O
O
H
3
O
+
!
OH
OH O
2
H
+







19.
20.
21.
22.
23.
Synthesis Problems 19-26:
N
O
O O
1.
2.
3. H
3
O
+
, !
SOCl
2
NaO
O
O O O
H
3
CO OCH
3
O
1. H
3
O
+
, !
2. !, -CO
2
excess
O
O
O
OH
O
O
1. H
3
O
+
, !
2. H
+
O
O
H
2
N NH
2
O O
1.
2.
3. CH
3
OH, H
+
K
2
Cr
2
O
7
SOCl
2
4. NaNH
2
O
O
O
1.
2. !, "C#
2
3. H
3
O
+
, ! H
+
O
O
O
COOCH
3








24.
25.
26.
27.
28.
29.
Br
O
O
O
1. Mg, CO
2
2. SOCl
2
3.
NaO
O
CN
Br
1. Mg
2. H
+
H
3
O
+
, !
O
CN
Br
NaOH
H
2
O,
H
+
O
O
HO
OH
O
HO
OH
O
1. H
+
3. CH
3
Br
2. LDA 4. H
3
O
+
, !
H
N
O
O
O
1. H
+
3. H
3
O
+
, !
2. LDA; CH
3
Br
O
O
O
O
1. LDA
2.
Br
H
3
O
+
! !
? =
HO
OH
O
? =
!
? =
? =
? =
? =




30.
31.
32.
33.
34.
O
1. LDA
2.
O
OCH
3
1. NaOCH
3
2. H
+
? =
O
O
HO
O
O
SOCl
2 NaO
O
LDA
O
O
? =
CH
2
COOCH
3
CH
2
COOCH
3
1. NaOCH
3
2. H
+
? =
O
O
OCH
3
H
3
CO OCH
3
O O
1. NaOCH
3
2.
O
1. LDA H
3
O
+
!
! -CO
2
? =
O
O
Name the followoing molecules using IUPAC nomenclature:
NH
2
O
benzamide
H
3
C N
H
O
NH
2
O
N-phenylethanamide 2-methylpropanamide





35.
36.
Name the followoing molecules using IUPAC nomenclature:
H
O
OH
H
3
C
O
OH
O
OH
H
C
O
OH
HO
OH
O
OH
O
Cl
O
OCH
2
(CH
2
)
6
CH
3
O
OEt
O
N
O
O
O O
O
O
Cl
O
O
N
H
O
OH
O
Cl
O
O
O O
Rank the following carboxylic acids derivatives in order of increasing reactivity toward
nucleophilic acyl-substitution reactions.
Formic acid or
Methanoic acid
Acetic acid or
Ethanoic acid
2,3-dimethylhexanoic acid
Prop-2-enoic acid 2-hydroxy Propanoic acid Benzoic acid
2-methyl Propanoyl Chloride octyl ethanoate
ethyl butanoate
N-methyl-N-propylethanamide
propionic anhydride
ethyl 2-chloro-2-phenylethanoate
Least Reactive
Most reactive
>
> >
>




37.
38.
39.
Explain the trend seen below:
Formla Name: CH
3
COOH ClCH
2
COOH Cl
2
CHCOOH Cl
3
CCOOH
Acetic
acid
Chloroacetic
acid
Dichloroacetic
acid
Trichloroacetic
acid
pKa: 2.86 1.48 0.70 4.76
Rank the following carboxylic acids from greatest to least acidic:
OH
O
Cl
OH
O
Br
OH
O
F
OH
O
F
F
F
A B
C D
Rank the following hydrogens in the following molecules in decreasing pKa:
H CH
3
O O
H
A
B
C
H
3
C OH
O O
H
A
B
C
HO OCH
3
O O
H
A
B
C
H
3
C OCH
3
O O
H
A
B
C
O
O O
O
O
OEt
O
O
O
OH O
O
H
3
C
O C
H
2
O
A
H
H
H
B
C
D
E
F
The trend reveals that the more electronegative atoms you add to the alpha position of the carboxylic acid, the more acidic that proton
becomes. This is due to the inductive effect of electronegative atoms, in that they pull electron density closer towards themselves thus
stabilizing the negative charge on the conjugate base of the carboxylic acid. The more electronegative atoms that are attached the
greater the inductive effect.
Most acidic Least acidic C > A > B > D
B > C > A C > B > A
A > B > C
B > A > C
C > F > B > D > A > E
Know the general Trends!
pKa ~ 9
pKa ~ 5
pKa ~ 16
pKa ~ 11
pKa ~ 13
pKa ~ 24



40.
RO
OR
OR
OR
Name the following molecules:
O
O
O
O O
O
Me
R
R
R
R
R
Just Kidding! GOOD LUCK ON THE EXAM!