1. a) Draw any five different correct molecular structures and calculate the following properties
using CHEMSKETCH software: Molecular formula, Formula weight, Composition of each
element, Molar refractivity, Molar volume, Density, Surface tension, Average mass.
b) Name these structures using and IUPAC rule. Explain how and using which relevant sub
rules, you get these names.
STRUCTURE 1:
CH3
C2H5
1-ethyl-2-methylcyclohexane
Molecular Formula
Formula Weight
Composition
Molar Refractivity
= C9 H18
= 126.239
= C(85.63%) H(14.37%)
= 41.70 ± 0.3 cm 3
Molar Volume
Surface Tension
Density
Average Mass
= 164.0 ± 3.0 cm 3
= 24.1 ± 3.0 dyne/cm
= 0.769 ± 0.06 g/cm 3
= 126.242899 Da
Molecule: 1 molecule of ethyl at first carbon,
1 molecule of methyl at the second carbon
Molecules’ name: 1-ethyl
2-methyl
Basic structure: cyclohexane
Name of structure: 1- ethyl-2- methylcyclohexane
STRUCTURE 2:
CH3
CH3
Molecular Formula
Formula Weight
Composition
Molar Refractivity
= C5 H10
= 70.133
= C(85.63%) H(14.37%)
= 23.25 ± 0.3 cm 3
Molar Volume
Surface Tension
Density
Average Mass
= 93.2 ± 3.0 cm 3
= 20.6 ± 3.0 dyne/cm
= 0.752 ± 0.06 g/cm 3
= 70.134944 Da
1,2-dimethylcyclopropane
Molecules: 2 molecules of methyl, 1 at first carbon,
and the other 1 at the second carbon.
Molecules’ name: 1,2-dimethyl
Basic structure: cyclopropane
Name of structure: 1,2-dimethylcyclopropane
STRUCTURE 3:
Molecular Formula
Formula Weight
Composition
Molar Refractivity
Molar Volume
Surface Tension
Density
Average Mass
CH3
H3C
1,3-dimethylcyclobutane
= C20 H40
= 280.532
= C(85.63%) H(14.37%)
= Not available
= Not available
= Not available
= Not available
= 280.539776 Da
Molecules: 2 molecules of methyl, 1 at first carbon,
and the other 1 at the third carbon.
Molecules’ name: 1,3-dimethyl
Basic structure: cyclobutane
Name of structure: 1,3-dimethylcyclobutane
STRUCTURE 4:
H3C
H3C
CH 2
CH3
CH 2
CH3
2,5-diethyl-1,1-dimethylcyclopentane
Molecular Formula
Formula Weight
Composition
Molar Refractivity
Molar Volume
Surface Tension
Density
Average Mass
Molecules: 2 molecules of ethyl, 1 at second carbon,
and the other 1 at the fifth carbon.
2 molecules of methyl, at first carbon
Molecule’s Name: 2,5-diethyl
1,1-dimethyl
Basic structure: cyclopentane
Name of structure: 2,5-diethyl-1,1-dimethylcyclopentane
STRUCTURE 5:
= C29 H58 ?2
= 406.771 + ?
= C(85.63%) H(14.37%) ?(0.00%)
= Not available
= Not available
= Not available
= Not available
= 406.782675 Da
Cl
CH3
1-chloro-3-methylcyclohexane
Molecular Formula
Formula Weight
Composition
Molar Refractivity
Molar Volume
Surface Tension
Density
Average Mass
= C36 H71 Cl ?2
= 539.402 + ?
= C(80.16%) H(13.27%) Cl(6.57%) ?(0.00%)
= Not available
= Not available
= Not available
= Not available
= 539.416359 Da
Molecules: 1 molecules of chlorine, at first carbon,
1 molecules of methyl, at the third carbon
Molecule’s Name: 1-chloro
3-methyl
Basic structure: cyclohexane
Name of structure: 1-chloro-3-methylcyclohexane
2. Using CHEMSKETCH draw an experimental apparatus used in any laboratory.
enough text captions with callouts to explain the apparatus and stages of protocols.
TITRATION APPARATUS
Burette Holder
0
10
20
30
Burette
40
50
Erlenmeyer Flasks
Support
Stand
3. Draw the following reactions.
Glycolysis-Conversion of Glucose to Fructose
Insert
ADP
CH 2-OH
O
HO
CH 2-O-P
CH 2-O-P
OH
O
ATP
HO
OH
O-H
OH
OH
H
O
OH
HO
OH
OH
Hemiacetal
Glu-6-P
enolization
CH2-O-P
H
O
CH 2-O-P
O
CH 2-O-P
OH
OH
OH
H
OH
CH2-OH
OH
HO
HO
CH 2-O-P
Ketolization
OH
OH
O
O-H
Fru-6-P
4. Draw five different reactions such as given above (taken from test books or written by you
correctly) with complete structural, stereo chemical (use the shaded or wedge bonds) and
mechanistic details (use the special type of arrows) using ChemSketch.
I. Reaction of the stereoisomeric 2,4-hexadienes with the dienophile maleic anhydride:
CH3
H
H
ether
+
O
O
2 h, 37' C
H3C
CH3
(2E,4E)-hexa-2,4-diene
O
H
H3C
O
O
furan-2,5-dione
H
O
(4R,7S)-4,7-dimethyl-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione
II. Reaction of conjugated dienes with alkenes:
O
CH2
H
C
H
COCH 3
C
H
H
CH 2
C
O
COCH 3
150°C
III. Enzyme catalyst:
O
H
C
C
O
-
O
fumarase
(an enzyme)
C
C
OH
-
+
H2O
H
O
O
CH
C
O
C
CH 2
O
-
-
malate
O
fumarate
IV. The Simmons-Smith Reaction:
H5C2
C2H5
C
+
C
H
H5C2
CH 2I2
H
H
H
methylene
iodide
cis-3-hexene
C2H5
cis-1,2-diethylcyclopropane
V. Ring-opening reactions under Acidic Conditions
H
H
O
+
H2SO4 catalyst
OH
CH 3OH
H
(±)-trans-2-methoxycyclohexanol
(82% yield)
5. Present a complete report of all the CHEMSKETCH exercises done during the lab hours.
CREATING STRUCTURE OF BICYCLO [2.2.2] OCTANE
(1s,4s)-bicyclo[2.2.1]heptane
bicyclo[2.2.2]octane
bicyclo[4.2.1]nonane
CREATING THE STRUCTURE OF A CYCLIC PEPETIDE
O
NH2
CH3
O
NH
O
HN
NH
NH2
O
CH3
O
HO
O
+
HN
O
N
H
Cyclic Tyr-Ala-Trp
N
H
Gramicidine S
DRAWING A REACTION SCHEME
+
DRAWING COMPLEX BIOMOLECULES
OH
OH
O
O OH
OH
O
O
H
HO
OH
OH
H
H
OH
O H
H
O
H
OH
HO
OH
OH
OH
OH
OH
H
β-Maltose
H
OH
β-Cellobiose
DRAWING VACUUM DISTILLATION APPARATUS
Thermometer.
Sign out from
instructor.
Water Out
Vigreux column
West condenser
Vacuum adapter
Water In
200 ml
round-bottom flask.
Immerse in heat bath.
H
Receiving flask.
Immerse in ice bath.
OH