Name: _ Date: 2/9/17
1) The carbon dioxide molecule is linear. The electronegativities of C and O are 2.5 and 3.5,
respectively. Based on these values and on consideration of molecular geometry, the C-O bond is
_ and the molecule is _.
A) polar; po
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. 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
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
The Midterm exam on Wednesday, March 8 includes 5 multiple choice questions
(each worth 1 point), 5 short answer questions (each worth 2 points), and you must
choose 3 out of 5 long answer questions (each worth 5 points).
Some Midterm Review
David Childster Christianity: A Global History (Chapter 1)
Andrew Walls The Missionary Movement in Christian History: Studies in the
Transmission of Faith
Christians of different time periods have different representative concerns
+ different heartlands
Physical change: A change that does not alter identity of a
substance or object, include shape, physical state, boiling
and freezing points, density, and color of the substance.
Chemical change: A change that does alter the identity of
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
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
have to accept that it does! If you want to find out more,
read about the wave nature of electrons.
Unlike an s orbital, a p orbital points in a particular direction - the one drawn
points up and down the page.
At any one energy level it is possible to ha
The orbital occupied by the hydrogen electron is called a 1s
orbital. The "1" represents the fact that the orbital is in the energy level
closest to the nucleus. The "s" tells you about the shape of the orbital. s
orbitals are spherically symmetric around
This page explains what atomic orbitals are in a way that makes them
understandable for introductory courses such as UK A level and its
equivalents. It explores s and p orbitals in some detail, including their shapes
and energies. d orbita
A 1s orbital holding 2 electrons would be drawn as shown on the
right, but it can be written even more quickly as 1s2. This is read as
"one s two" - not as "one s squared".
You mustn't confuse the two numbers in this notation:
The order of filling orbital
Note: Some UK-based syllabuses will eventually want you to
be able to draw, or at least recognise, the shapes of d
orbitals. I am not including them now because I don't want to
add confusion to what is already a difficult introductory topic.
Check your sy