REVIEW SHEETS

 

TEST 1 MATERIAL

TEST 2 MATERIAL

TEST 3 MATERIAL

TEST 4 MATERIAL

 

 

 

 

**** TEST 1 MATERIAL ***

 

Review of organic chemistry, week 1

9/1/06

 

  1. Sketch the currently accepted model of atomic structure.  Include how electrons are organized around the nucleus.

 

  1. What makes an atom of carbon different from an atom of nitrogen?

 

  1. What is atomic number, mass number and atomic mass?

 

  1. How are the elements organized on the periodic table and what trends arise as a result of that organization?

 

  1. Which electrons are involved in bonding?

 

  1. How many bonds would you expect the following elements to form and why?

 

    1. chlorine
    2. carbon

 

 

Review of organic chemistry, week 2

Sept 6 – 8, 2006

 

By the end of class on Sept. 8, you should be able to answer the following types of questions and perform the following tasks:

 

1.  Define and/or calculate: Isomer, formal charge, VSEPR, vector addition, electronegativity, polarity, resonance, valence bond theory, hybrid orbital

 

2. Identify the one unifying idea that all of organic chemistry builds upon

 

3. Predict the polarity of a molecule by working through the following steps:

            A. Drawing a Lewis structure

            B. Determining molecular shape

            C. Determining bond polarity

            D. Determining polarity of a molecule.

 

4. Calculate formal charge

 

5. Identify covalent, polar covalent and ionic bonds

 

6.  Be able to easily translate expanded, condensed and line structures.

 

 

Review organic chemistry, week 3

9/15/06

 

By the test next Friday, you should be able to:

 

Perform the tasks outlined in the summaries of weeks 1 and 2.

 

Resonance

1)     Define resonance structures.

2)     Explain the need for resonance structures.

3)     Distinguish between resonance structures and isomers.

4)     Use curved arrow notation to show how electrons differ between structures.

5)     Propose resonance structures and identify which are the most important.

 

 

Valence bond theory

1)     Describe our valence bond model, what it can predict, and its limitations.

2)     Describe the need for hybrid orbitals.

3)     Define hybrid orbital.

4)     Predict the hybrid orbital and types of bonding (σ and π) in a given bond.

5)     Explain how %s character determines bond length and strength.

 

 

Acids and Bases

1)     Define Bronsted-Lowry and Lewis acids and bases.

2)     Define proton, hydrogen, hydride, hydroxide, hydronium, Ka and pKa.

3)     Distinguish between strong and weak acids and bases by Ka or pKa.

4)     Compare the relative acidity of two compounds.

5)     Use curved arrow notation to show flow of electrons in an acid/base reaction. (not on first test)

6)     Predict relative solubility of charged and uncharged species.

 

***TEST 2 MATERIAL***

 

Organic chemistry review week 4

9/29/06

 

You should be able to:

 

1) Predict the most acidic proton in a molecule and the most acidic molecule in a group. 

2) Clearly rationalize your choice of most acidic proton/molecule based on differences in elements, inductive effects, resonance and hybridization.

3) Determine the direction of equilibrium of an acid/base reaction given the pKas of the acid and conjugate acid.

4) Use curved arrow notation to show flow of electrons in any reaction.

5) Define functional group.

6) Identify functional groups in any molecule (you need to memorize the functional group names – make flash cards if they help you).

7) Recognize the importance of functional groups in molecules.

8) Identify and distinguish between van der Waal’s forces, dipole-dipole interactions and hydrogen bonding.

9) Explain what changes occur at the molecular level when materials change phase.

10) Predict relative solubility and melting point and clearly rationalize your answer.

11) Understand the relevance of intermolecular forces in biologically relevant molecules and their interactions.

 

 

O. chem. review sheet

Week 5, 10/06/06

 

Be the end of this week, you should be able to

 

  1. Predict the solubility of molecules in water and organic solvents
  2. Understand how deprotonation of an acid or protonation of a base effects solubility in water
  3. Explain how soap cleans
  4. Explain how molecule structure leads to the phospholipid bilayer and micelle shape
  5. Explain how ionophores transport charged species across the cell membrane
  6. Explain the roles and importance of the cell membrane
  7. Calculate degree of unsaturation for hydrocarbons
  8. Be able to quickly draw isomers based on the degree of unsaturation
  9. Label primary, secondary, tertiary Cs and Hs
  10.  Name alkanes and cycloalkanes
  11.  Recite the parent chain names of alkanes with 1 to 10 carbons
  12.  Distinguish between cis and trans isomers and be able to name cycloalkanes as cis or trans
  13.  Define stereoisomer and conformer
  14.  Use Newman projections to draw staggered and eclipsed alkanes

 

O. chem. review sheet

Week 6, 10/13/06

Be the end of this week, you should be able to:

1. Define steric strain, torsional strain, angle strain and 1,3-diaxial interactions.

2. Identify different types of strain in molecules.

3. Determine the most stable conformation of an alkane.

4. Use energy costs of interactions to construct a graph of strain energy as a function of conformation.

5. Predict the percent population of a particular conformation based on differences in energy and ΔGº=-RTlnKeq

6. Draw cyclohexane in the chair conformation.

7. Ring flip a model of cyclohexane and substituted cyclohexane.

8. Draw two conformations of substituted cyclohexanes.

9. Determine which conformation of a substituted cyclohexane is most stable and rationalize your choice by referring to figures of the cyclohexanes.

10. Write a balanced combustion reaction.

11. Distinguish between oxidation and reduction.

12.  Recognize how the organic chemistry shortcut of determining oxidation and reduction is based on electron loss and gain.

13. Identify different classes of lipids.

14. Distinguish between unsaturated and saturated fatty acids.

15. Compare physical properties of unsaturated and saturated fatty acids.

16. Understand action of analgesics.

17. Identify the nucleophile and electrophile in reactions of lipids.

18. Explain why Olestra is not metabolized.

 

***TEST 3 MATERIAL***

 

 

O. chem. review sheet

Week 8, 10/27/06

 

By the end of this week, you should be able to:

    1. Identify chiral and achiral objects.
    2. Be able to superimpose molecules.
    3. Label stereocenters.
    4. Draw a mirror plane through a molecule.
    5. Connect the idea of symmetry and achirality.
    6. Identify enantiomers and meso compounds.
    7. Recognize the importance of enantiomers in the body.
    8. Draw enantiomers.
    9. Name stereocenters R or S.

 

 

O. chem. review sheet

Week 9, 11/3/06

 

 

By the end of this week, you should be able to:

  1. Define: absolute configuration, relative configuration, chirality, stereogenic center, optical activity, observed rotation, specific rotation, enantiomeric excess, diastereomer and enantiomer.
  2. Assign absolute configuration.
  3. Identify sets of molecules as enantiomers, diastereomers, constitutional isomers, conformers.
  4. Calculate how many stereoisomers are possible for an optically active molecule.
  5. Understand significance of d/l and +/- and connection to R/S.
  6. Explain connection between optical activity and chirality.
  7. Draw enantiomers and diastereomers.
  8. Calculate ee.
  9. Understand how stereoisomers differ when undergoing physical changes and chemical changes.
  10.  Explain how optical activity led to the discovery of tetrahedral carbon.

 

 

 

Organic chemistry review

Week 10

Nov. 10, 2006

 

By the end of this week, you should be able to:

 

(1)   Understand the importance of spectroscopy and spectrometry and the role of the techniques in the laboratory.

(2)   Differentiate between spectroscopy and spectrometry.

(3)   Define and/or identify the following on a mass spectrum:  base peak, molecular ion peak, m/z, relative abundance, low-res and high-res GC, GC/MS

(4)   Propose reasonable structures from a mass spectrum by

a.      Proposing reasonable molecular formulas from a molecular ion peak.

b.      Proposing possible structures from the molecular formulas.

c.      Eliminating unreasonable structures bases on fragmentation.

(5)   Define the following in terms of electromagnetic radiation: photon, energy, wavelength, frequency

(6)   Define quantized energy states and vibrational modes.

(7)   Explain how quantized energy states lead to the emission or absorption of light.

(8)   Match particular quantized energy states (electronic transitions in atoms/molecules, vibrational modes) to the part of the electromagnetic spectrum that they absorb/emit.

 

 

 

****TEST FOUR MATERIAL****

 

Organic chemistry I

Review of week 12

Nov. 30 2006

 

By the end of the week before break, you should have been able to:

 

(1)   Use IR to identify functional groups in molecules.

(2)   Connect modes of vibration to IR bands.

(3)   Identify symmetric modes of vibration that do not appear in IR.

(4)   Use IR together with MS data to propose reasonable structures.

 

By the end of this week you should be able to:

(1)   Explain how odd numbered nuclei behave in a magnetic field.

(2)   Understand how frequency and field strength are connected in NMR.

(3)   Predict the number of 1H-NMR signals that a given molecule is expected to have (i.e. count the different types of protons in a molecule).  Don’t forget that diastereotopic protons have different signals.

(4)   Predict the relative deshielding of protons in a molecule (i.e. which proton will be most deshielded, which will be least, etc).

(5)   Use signal position, integration and multiplicity to piece together the structure of a molecule.  You must use a data table to do this:

 

PPM

Integration

Multiplicity

Assignment

 

 

 

 

 

 

 

 

 

 

Organic Chemistry I

Review of Week 13

Dec. 8, 2006

 

By the end of the week, you should be able to:

  1. Interpret 13C-NMR spectra.
  2. Identify conjugated molecules and assess relative absorption of UV/vis light.
  3. Explain how highly conjugated molecules are intensely colored.
  4. Categorize reactions as substitutions, additions and eliminations.
  5. Define reaction mechanism, concerted reaction, stepwise reaction, homolysis, heterolysis, homogenesis, heterogenesis.
  6. Identify which bonds are broken and which are formed over the course of a reaction.
  7. Interpret reaction diagrams in terms of enthalpy.

 

 

Organic Chemistry I

Review of Week 14

Dec. 15, 2006

 

By the end of the week, you should be able to:

1. Estimate ΔHº for a reaction using bond dissociation energies.

2. Understand the significance of ΔGº= ΔHº - TΔSº.

3. Calculate Keq from ΔGº using ΔGº=-RTlnKeq.

4. Interpret reaction diagrams including: determining extent of reaction, the relative rate of steps, how many steps are in a reaction, whether the reaction is exo- or endothermic, identifying intermediates and transition states.

5. Write a rate law given a reaction mechanism.

6. Use collision theory to predict how a change in concentration, temperature or other factor will change a reaction rate.