Grossmont Cuyamaca Community College District Organic Structures Worksheet

  

Description

– Whole worksheet needs to be filled out

– Must have common knowledge of organic chem

– Hand writing/ typing must be legible

Review & Drawing Organic Structures
Part I. The “Beginning”
A) Write the chemical formula and chemical name for any one ionic compound.
B) Write the chemical structure of a molecule/compound that contains covalent bond(s).
C) What is the difference between ionic and covalent compounds?
Part II. Formal Charges
A) Identify any formal charges in the compounds below.
H
H
O
H
Al
H
C
H
H
H
H
H
H
C
H
H
H
B) Phenylalanine is an amino acid that is essential to human nutrition. The representation below
shows the structure of phenylalanine at physiological pH (7.35). Consider this structure to answer the
following questions
1. The formal charge on oxygen A is ______. (Show calculation ___________________)
2. The formal charge on oxygen B is ______. (Show calculation ___________________)
3. The formal charge on nitrogen is _______. (Show calculation ___________________)
BH4–
A
B
O
NH3
ne
en
a
an
h
l
l
i
p
y
A. Draw the structure for each of the following ions; in each, indicate which atom
possesses the formal charge.
H3O+
NH2–
OCH3–
NH4+
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O
Part III. Polarity (Bond polarity, Molecular Geometry, Molecular Polarity)
A. For each of the compound below, identify any polar covalent bonds by drawing bond dipole arrows
(
) in the appropriate locations. A Pauling electronegativity chart is included in the appendix of
this manual.
O
O
H
H
C
Mg
H
H
C
Br
C
H
H
C
C
H
H
C
C
H
H
H
Cl
H
O
C
H
H
H
C
H
H
H
B. For each compound below, 1) Identify any polar covalent bonds, and indicate the direction of the
bond dipole moment using the crossed arrow convention (
). 2) Identify the molecular geometry
around the center atom(s). 3) State whether the molecule is polar (net dipole) or non-polar (no net
dipole).
(1)
CO2
(2)
CH2O
(3)
CCl4
(4)
CH3CH2CH3
5)
HCCH
6)
NH2CH3
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Part IV. Lewis Structures of common solvents used in this class. Fill in the chart below with the
appropriate Lewis structure for each molecule. Determine the polarity of the molecule and look up
the density.
Miscible or
Dipole
Density
Condensed
Chemical Name
Immiscible in
Lewis Structure
Moment
(in
Formula
(common name)
Water (see
(see Index)
g/mL)
Index)
CH3CH2OH
ethanol or (ethyl
alcohol)
CH3OH
methanol or
(methyl alchohol)
CH3COCH3
CH2Cl2
2-propanone or
(acetone)
Dichloromethane,
DCM or
(methylene
chloride)
H2O
CH3(CH2)4CH3
hexane
CH3CO2H
acetic acid
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Condensed
Formula
Lewis Structure
Chemical Name
(common name)
CH3CO2CH2CH3
ethyl acetate
CH3CN
acetonitrile
CHCl3
chloroform
CH3CH2OCH2CH3
ethoxy ethane
(diethyl ether)
Dipole
Moment
Miscible or
Immiscible in
Water
Density
Part V. Polarity Ranking. Organize the following compounds from least polar to most polar: hexane,
ethyl acetate, dichloromethane, methanol.
Nonpolar
___________ _____________ _____________ ____________
Most polar
Part VI. Analysis of Dipole Moment and Miscibility with Water. What can you conclude from the
dipole moment of the organic solvents in the table and their resultant miscibility or immiscibility in
water? Are there any anomalies? Explain.
Part VII. Solvent Density and Structure. Look at the structure and the density of the organic solvents
that are immiscible with water. Compare with the density of water (i.e. which are more dense or less
dense than water?). What can you conclude about how the structure of the solvent affects its
density?
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