EXPERIMENT #1 (Monday Feb. 3rd and Friday Feb. 7th):
PART 1: Purification and Characterization of Acetanilide
PART 2: Design and Execution of a Purification Strategy
Part 1 is derived from Gilbert, J. C., Martin, S. F., Experimental Organic Chemistry, A M
1. Optical rotation (), i.e. the amount plane polarized light is rotated when
it goes through a chiral sample at a specic temperature and wavelength, is
used to discriminate enantiomers and to examine the optical purity of a
1. Cyclopentane (C5H10): Ring strain = ~6.5 kcal/mol, forms envelope
(know how to draw) or twist conformations (these are ~equal energy) have
2 eclipsing H interactions, mostly staggered, ~108 bond angle, close to
1. Know what the common names isopropyl, isobutyl, sec-butyl and tertbutyl mean (i.e. if I give you the name, be able to draw the structure).
However, when I ask for the IUPAC name, I expect the IUPAC not these
1. Know how to draw the energy diagram for butane and related molecules.
Label using dihedral angle and starting at 0.
2. Alkenes: contain a double bond. The double bond consists of a
(sigma) bond (Csp2-Csp2 ) and a (pi) bond (C2p-C2p). K
1. Molecular orbitals are made from combinations of atomic orbitals.
2. Rules that govern MO theory:
a.) ! Conservation of orbitals (i.e. n atomic orbitals gives n molecular
b.) ! Molecular orbitals are arranged in order
1. Hybridization: Combination of the atomic orbitals of the valence shell
(Typically 2s, 2px,2py,2pz) on a single atom to make hybrid atomic orbitals
that can be used to more accurately describe the structure and properties
of a molecule.
1. Octet Rule: Atoms react to achieve a noble gas conguration (i.e. 2
valence e- for H, 8 e- for other atoms). Note: Atoms in Row 2 elements (B,
N, C, O, F) cannot have more than 8 electrons surrounding them (this
means no more than 4 bond
1. Covalent bonds are formed by sharing a pair of electrons between two
atoms. Many covalent bonds are polarized (meaning one of the atoms has
more of the electron density from the bond than the other). The relative
1 Chiral Center: A tetrahedral atom (usually Carbon but not always) that
has 4 different substituents attached to it. Also called a stereogenic center.
Most (not all) chiral molecules have one.
2. Meso Compound: A molecule that contains 2 o
1 Carbocation stability :
Rationale for effect of alkyl substituents:
1. Inductive effect. -bond effect, positive charge is
stabilized through induced di
Question of the Week 6:
Based on our in class discussions of what effects the pKa, explain the following: substitution with
oxygen vs. sulfur has different effects on the pKa in the two sets of molecules shown below. In one
case, you see a higher pKa with
Question of the Week 5
a. Draw the planar form of (1S, 2R) 1-methyl-2-propyl cyclohexane.
b. Draw the two possible chair conformations of the above molecule and circle the most stable
c. Using the Table 5.3, estimate the relative number o
QOTW 2: Spring 2014
a. Draw the molecular orbital (MO) diagram for the combination of 2 hydrogens to form H2-.
Label the bonding and antibonding orbitals and draw them.
b. Will this molecule form? Why or why not? (Explain in no more than 2 sentences).
Question of the Week 1: Draw all Lewis Dot Structures for the following molecules (i.e.
resonance structures if they exist). In some cases the connectivity of the atoms is shown. Where
there are resonance structures, circle the most important one. Note: t
1. Know IUPAC nomenclature for alkyl halides, alcohols, amines, ethers,
thiols and thioethers. For ethers and amines, be able to recognize the trivial
naming system as well as it is widely used.
2. Alkyl halide: Has structure R-X, where R=
1. Cyclohexane (C6H12): Ring strain is negligible. Most stable
conformation is the chair form (see below). In it all H are staggered. Know
how to draw a proper chair structure. Substituents can be axial or equitorial
on the chair (see belo
1. Addition of H-X across an alkene: Our rst reaction. An example of the
chemistry is given below.
Mechanism of the Addition Reaction:
: Br :
This reaction can also occur with HCl and HI.
2. Nucleophile: speci
1. Bond lengths and strengths. Know the following:
C-C * and
C-C* and 2
1. Rules for Ranking and Identifying Important Resonance Structures.
The rst rule (RULE A) is the MOST IMPORTANT. If more than one
structure follows rule A, the more of the other preferences a structure
follows, the more important it is (i
Experiment #2: Extraction
(Monday Feb. 10th - Friday Feb. 14th)
PART 1: Separation of Naphthalene and Benzoic Acid by One-Base Extraction
PART 2: Design and Implementation of an Extraction to Separate a Mixture
Part 1 is derived from Gilbert, J. C., Marti
MOLECULAR MODELING: Post-
1. Using 2D chemdraw software, draw all possible Newman projections of 2-
methylpentane looking down C2-
C3 bond and indicate structures with
highest and lowest energy conformatio