Download 110A Exam 1 Review Sheet-Fall Semester 2016 Review Session

110A Exam 1 Review Sheet-Fall Semester 2016
Review Session: Wednesday, September 14th, 7:00 PM, SN Aud
Chapter 1:
1. Be familiar with an example of a biologically active organic molecule and an interesting aspect of
its history.
2. Be able to explain Wohler’s and Kolbe’s contribution to the demise of vitalism.
3. Be able to explain Couper, Kekule, and Butlerov’s contributions to the structural theory of
organic molecules.
4. Be able to list the usual valences of H, O, N, S, P, F, Cl, Br, I, and C, and to know examples of
cases where carbon’s valence is not four.
5. Be able to list and apply a set of rules of evaluating resonance structures and gauging their
relative contributions to the overall electronic structure of a molecule.
6. Be able to write valid Lewis structures and assign formal charges in small molecules.
7. Be able to apply VSEPR theory to a molecule and explain a case where theory is accurate and a
case where the theory is not.
8. Be able to write down the atomic orbitals for any first-row atom, using C as an exemplar.
9. Be able to form orbital hybrids of atomic orbitals to account for the typical geometries seen for
carbon and other first-row atoms (sp, sp2, sp3).
10. Be able to draw an orbital energy diagram for a single bond, showing the formation of the 
bonding orbital and the * antibonding orbital.
a. To associate the concept of rapid rotation about the single bond at room temperature.
b. To be able to visualize the spatial co-existence of the  and * orbitals.
11. Be able to draw an orbital energy diagram for a  bond, showing the formation of the  bonding
orbital and the * antibonding orbital.
a. To associate the concept of hindered rotation about the  bond at room temperature or
when little light is present.
b. To be able to visualize the spatial coexistence of the  and * orbitals.
12. To be able to explain what constitutes a polar covalent bond, and to use the convention for
assigning bond and molecular dipole moments.
13. To retain exemplars of polar and nonpolar compounds, and to be able to explain the factors
(bond polarity, symmetry properties) governing their polarity.
14. To translate a condensed structural formula into a bond-line formula, and vice-versa.
15. To provide a definition of the term constitutional isomers and to retain an exemplar set.
Chapter 2
1. To be able to identify the commonly encountered organic functional groups, and to:
a. Be able to diagnose 1, 2, and 3 alcohols or halides.
b. Be able to diagnose 1, 2, 3, and quaternary amines.
c. Be able to diagnose cis and trans isomerism in alkenes.
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2. To be able to explain the basis for defining a solvent as protic or aprotic, as polar or nonpolar,
and to retain exemplars of each of the four descriptor combinations.
a. To be able to write an equation relating the system’s energy as a function of two
charges, their intervening distance, and the medium’s dielectric constant.
b. To retain an exemplar of a high dielectric and low dielectric solvent, and to explain their
structural features and interactions with charged (ionic) substances and nonpolar
substances.
3. To be able to accurately draw a bonding picture of methane, ethane, ethylene, and acetylene,
by inscribing the appropriate orbital hybrids on a geometrically correct skeleton. To then be able
to do the same for any combination of other first-row elements and their compounds.
4. To be able to explain the different types and origins of intermolecular forces, retaining an
exemplar of each:
a. Ionic.
b. Ion-dipole.
c. Dipole-dipole.
i. Hydrogen bonding.
d. Van der Waals (attractive). Be able to explain an instance where this IMF is used in
biology and how researchers tested the hypothesis that it was.
5. Be able to explain the criteria at the molecular level for allowed infrared (IR) transitions, and:
a. be able to write an expression relating the vibrational frequency to the force constant
(bond strength) and masses of the atoms directly involved in the vibrational mode.
b. Be able to explain the reasons (dipole moment magnitude & number of contributing
bonds) why some IR transitions are larger than others.
6. Be able to identify candidate compounds using an IR spectrum and table of absorption
frequencies.
Chapter 3
1. Be able to explain the Lewis and Bronsted acid-base definitions, and be able to identify species
as such.
2. Be able to identify and label acid-base species as the conjugate acid or conjugate base.
3. Be able to compute the pH of an aqueous weak acid solution.
4. To be able to write the Henderson-Hasselbalch equation and use it to predict the percent
composition of ionized and unionized species at a given pH.
a. To retain an operational definition of pKa: the pH at which a species is half-ionized.
5. To explain the structural factors affecting acidity: electronegativity, hybridization, resonance,
and inductive effects.
6. To retain a set of representative pKa values for a range of commonly-encountered
molecules/species, such as:
a. HCl
b. Hydronium ion
c. Acetic acid
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7.
8.
9.
10.
d. Ammonium ion
e. Water
f. Alcohols
g. Acetylene
h. Hydrogen
i. Ammonia
j. Ethylene
k. Methane
To explain how acidity (ionization) can be affected by solvent.
To explain why water can’t be present for many organic acid/base reactions, i.e., to be able to
explain the leveling effect.
a. To be able to predict the outcome of acid-base equilibria on the basis of knowing two
pKa values. (acid-base reactions always favor the formation of the weaker acid and
weaker base)
To be able to use the arrow notation for writing the mechanism of a base reacting with an acid.
To be able to propose a synthesis of an acetylene derivative deuterated at the C1 position.
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