CH221 Organic Chemistry 1
Worksheet and Summary Chapter 1
LO: Derive electronic configuration diagram of atoms/ions
1. Provide electronic configurations of each atom or ion provided. Identify valence electrons and orbitals for
each species.
oxygen atom chloride ion potassium ion sodium atom
LO: Draw atomic orbitals with planar and/or spherical nodes where necessary
2. Sketch a 4p orbital and a 5s orbital, labeling all peaks (+), toughs (-), and nodes (- - - - -).
LO: Draw Lewis structures and identify whether a Lewis structure is acceptable or not
3. Which is an acceptable Lewis structure for diazomethane, CH2N2?
a. b. c. d.
4. Draw two reasonable Lewis structures with molecular formula C2H6O, and one Lewis structure with the
molecular formula C2H3Cl. In all cases, assume that all bonding adheres to the octet rule and that there are no
formal charges.
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LO: Identify ionic compounds based on formula
5. Indicate on the lines whether the following pairs of atoms be most likely to form ionic or covalent bonds.
K and Br H and C C and O H and N Al and O
6. Which of the following compounds have completely ionic bonds:
CCl4 HCl NaAt K2 CS2 CsF HF XeF2 BF3
LO: Identify/calculate the formal charge of a specific atom in a structure
7. Compute formal charges on the following structures. Calculate the charge on the entire structure.
LO: Evaluate whether resonance structures are equivalent or not equivalent
8. The allyl cation can be represented by the following resonance structures:
Are they equivalent structures? How do you know?
Sketch a resonance hybrid of the allyl cation in the box to the right:
Although the preceding structures are reasonable descriptions of the allyl cation, the following cation
cannot be described by analogous resonance structures. Explain why the structure on the right is not a
reasonable resonance structure.
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9. Benzene is known to have 6 identical carbon-carbon bonds, with equal lengths and equal strengths. Draw a
resonance structure that explains these empirical data.
10. Given here are resonance structures of the carbonate ion. How much negative charge is on each oxygen
atom in the ion? What is the bond order of each carbon-oxygen bond in the ion?
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LO: Predict relative bond lengths and bond strengths
11. Rank the following 4 bonds in terms of their bond length. Write the number 1 below the shortest bond,
and the number 4 below the longest bond. Fill in numbers 2 and 3 appropriately.
C=C C=O O-H C-H
12. Circle the stronger bond in each of the following pairs.
C-C vs C=C H-H vs H-O C=O vs C=C C-C vs C-Cl C≡N vs H-N
13. Based on the given structure, choose the correct letter to answer the following questions.
Which bond is longer? b or d
Which bond is shorter? c or d
Which bond is stronger? a or f
Which bond is weaker? g or h
LO: Approximate bond angles, determine geometry, and draw molecules in 3D
14. Predict the approximate bond angle and geometry of central atoms in the following compounds. Drawing
the Lewis structures is a good way to start.
BF4- H2C=O H3C-C≡N
15. Draw three different, but equivalent, line and wedge structures of dichloromethane, CH2Cl2.
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LO: Derive hybridized atomic orbitals for carbon, nitrogen, or oxygen
16. Construct a hybrid atomic orbital diagram for the hydronium ion (H3O+), using oxygen sp3 hybridized
orbitals. Start with the atomic electronic configuration for the O+ ion.
17. Construct a hybrid atomic orbital diagram for the boron atom in BF3. Then sketch the molecule with line
and wedge format, and depict the unhybridized p orbital on the structure.
LO: Identify hybridization of specified atoms in a structure
18. Select row a, b, c, or d: The hybridization of the numbered carbon atoms in the following compound is best
described as:
1 2 3 4
a. sp2 sp3 sp sp2
b. sp2 sp3 sp2 sp
c. sp3 sp sp3 sp
d. sp2 sp2 sp sp2
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LO: Draw MO diagrams with atomic orbitals and appropriate electrons. Calculate bond order based on MO
diagrams
19. Draw an orbital interaction diagram (MO diagram) of the H2+ ion. Is this species likely to exist, or would it
dissociate into separate atoms?
20. If the bond dissociation energy (a measurement of bond strength) of H2 is 435 kJ/mol, estimate the bond
strength of H2+.
21. Calculate the bond order of H2+.
LO: Identify polar covalent bonds, as opposed to covalent or ionic bonds
22. Indicate on the lines whether the following pairs of atoms be most likely to form covalent or polar covalent
bonds.
C and Br H and C C and O H and N C and S
LO: Use molecular geometry to determine molecular polarity
23. Which of the molecules in problem #14 above are likely to have an overall dipole moment?
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24. Analyze the polarity of each bond in the given structure. Which bond, other than the C-C bond, is the least
polar? Which carbon atom contains the highest partial positive charge?
LO: Understand different molecular locations of formal charge and actual charge
25. For which ion does the formal charge give a fairly accurate picture of the location of the actual charge? Be
sure to draw the Lewis structures.
