CHAPTER 8 - Practice Exercises (ORGANIC CHEM I )
1. Give IUPAC names for the following compounds.
Br C C - CH
2
- CH
3
________DR. PAHLAVAN b) a) CH
3
- CH
2
- C C - CH - CH
2
- CH
3
C CH c)
CH
2
- CH
3 e)
CH
3 d) H
2
C = CH - CH = CH - CH - C
H C
CH
CH
C = C f)
H g)
C C h) CH
3
(CH
2
)
3
C C (CH
2
)
3
CH
3 i) j)
2. Draw structures corresponding to the following names;
a) 4- Bromo-3,3-dimethyl-1-hexen-5-yne
c) 2,5,5- Trimethyl-3-heptyne
e) 2,4- Octadiene - 6 – yne
b) Ethynylcyclopentane
d) 3,6-Heptadien -1 – yne
f) Diphenyethyne(diphenylacetylene)
g) 3-sec- butyl-1- heptyne
i) Trans-1,2-diethynylcyclohexene
h) Decyne
j) 1,3,5 - heptatriyne
3. Synthesis the following compounds using 1-pentyne as the only source of carbon along with any inorganic
reagents you need. More than one step may be needed. b) 3,4-dichloroheptane a) 2-hexanone
1

4. Predict the products of the following reactions;
CHBr-CH
2
Br a)
2 KOH ethanol b) CH
3
-CH
2
- C C -CH
3
H
2
Lindlar catalyst c) CH
3
-CH
2
- C C -CH
3
NH
4
Cl/CH
3
COOH e) g) i)
C
C
C
CH
CH
CH
HCl
HBr
1 equivalent
HgSO
4
/H
2
SO
4
H
2
O
HBr/ 2 eq
CH = CH - C C-H
H
2
, Pd/ C d) CH
3
-CH
2
- C C -CH
3
Li/NH
3 or Na/NH
3 f) CH
3
-CH
2
- C C -H
1)
NaNH
2
2) C
6
H
5
Br h) j)
C CH
1) BH
3
, THF
2) H
2
O
2
, OH
C CH
1) NaNH
2
/NH
3
2) CH
3
CH
2
I k) l)
KMnO
4
H
3
O m)
O
3
H
3
O
5. Predict the products from the reaction of following compounds with the following reagents;
I) 1- pentyne II) 2-heptyne III) cyclohexyne
a) 1 eq. HBr b) 1 eq. Br
2 c) H
2
/ Lindlar catalyst d) Li in NH
3
e) Excess Br
2 f) 2 eq. HCl g) Excess H
2
, Pd/C h) HgSO
4
, H
2
SO
4
/H
2
O
i) NaNH
2
in NH
3
/ CH
3
CH
2
Br j) BH
3
, THF and H
2
O
2
, OH
–
6.
Compound A (C
9
H
12
) on catalytic hydrogenation over a Pd/C, absorbs 3 equivalents of H
2
to give compound B (C
9
H
18
). Ozonolysis of compound A gave a ketone, that was identified as cyclohexanone.
Compound A also reacts with NaNH
2
/NH
3
followed by addition of CH
3
Br gave compound C(C
10
H
14
).
What are the structures of A, B, and C.
2

7.
Identify structures for compounds A, B, C, D, E and F.
HgSO
4
, H
2
SO
4
C
9
H
8
Compound A
2 moles H
2
Mixtures E and F
O
3
/H
3
O ozonolysis
Compound B
Compound C and D
Carboxylic acids
8.
How would you carry out the following reactions (identify reagents).
H
CH
3
?
a) CH
3
- C C - CH
3
C = C
H CH
3
O b)
?
CH
2
- C C - H CH
2
- C - CH
3 c)
C C - CH
3
?
d) CH
3
CH
2
CH
2
CH
2
C C - CH
3
O
C - OH +
O
OH
C - CH
3
?
CH
3
CH
2
CH
2
CH
2
CO
2
H + CH
3
- CH
2
COOH e) H- C C- H f) g) i)
?
?
O
H - C C - CH
2
- CH
3
O
HO - C - (CH
2
)
4
- C - OH
?
H
2
C = CH - CH
2
- CH
3
?
CH
2
Br - CH
2
- CH
2
- CH
3
O
?
C C - H
?
CH
2
- C - H
O j)
CH
3
- CH
2
- C C - CH = CH
2
?
3
CH
3
- CH
2
- C C - CH
2
- CH
3

9.
How would you carry out each of the following synthesis. Each reaction required more than one step.
Using acetylene and any alkyl halides as starting materials synthesis the folloewing compounds.
O a) (CH
3
)
2
CH- CH
2
CH
2
CH
3 b) CH
3
- C -OH
C = C
H
H c) CH
3
- CHBr - CHBr - CH
3
O d) CH
3
- CH
2
- CH
2
- CHBr - CH
3 e) CH
3
- C - CH
2
- CH
2
- CH
2
- CH
2
- CH
3 f) CH
3
- CH
2
- CH
2
- CHOH - CH
2
Br
10.
Show reagents and experimental conditions required to bring about the following transformations.
Identify 1 –11.
CH
3
- CH
2
- CH
3 CH
3
Br
(1)
C = C
O Br
CH
3
CH
3
- CH - CH
3
H
Br
CH
3
- C - CH
2
- CH
3
CH
3
C = C
(9)
(2)
(8)
(10)
CH
3
CH
3
CH
3
- CH = CH
2 (11)
H
CH
3
CH
3
- C C - CH
3 C = C
(3)
Cl
(7)
Br
H
(4) (5) (6)
CH
3
- CH - CH
2
CH
3
- C C - H
H
3
C - C = CH
2
CH
3
- C - CH
3
Cl Cl Cl
Cl
11.
Alkene vs. alkyne selectivity- Provide the product for each reaction. Pay close attention to
regioselectivity, stereoselectivity, and chemoselectivity. This exercise is for one functional group vs.
another functional group.
A
L
1 eq. Br
2
CCl
4
B
2 eq. KMnO
4
NaOH/H
2
O
Li/NH
3
K
CH
2
I
2
, Zn(Cu)
C ether
H
3
C - CH - CH = CH
2 excess, H
2
SO
4
HgSO
4
H
2
SO
4
/H
2
O 2 eq. Br
2
J C CH
D
CCl
4
I
1 eq. HBr ether
2 eq. HBr ether 1) NaNH
2
2) CH
3
Br
H
2
/Pd (C)
H
H
2
Lindlar
G
F
E
4