Frequently Asked Questions about the ACS Standardized Exam

What is the ACS Standardized Exam?

As described in the syllabus, the final exam for this course is the American Chemical Society (ACS) standardized exam in organic chemistry. The exam covers the entire year of introductory organic chemistry, and allows your instructor to gauge your performance in the course relative to students across the nation.

Are there sample questions available?

YES. A study guide is available. It should be available in the bookstore. If it is not, you can obtain a mail-in order form (.pdf Adobe Acrobat format) for copies from the following web address:

http://www.uwm.edu/Dept/chemexams/


When the page opens, select "Assessment Materials", and at the bottom of the new page, select "Organic Chemistry Official Study Guide." The cost (2002) is $15 plus $6 shipping. If you mail in an order, allow 21 days to receive the book.

What is the format of the ACS Standardized Exam?

The test consists of 70 multiple-choice questions. You will have exactly two hours to complete the exam. Since this is a standardized exam, the conditions of the exam are quite specific. For example:

What should my strategy be?

Your score is based on the number of questions you answer correctly. There is no penalty for incorrect answers. Therefore it is to your advantage to answer every question - even if you have no idea which answer is correct.

How should I study for this exam?

Use your exams and quizzes from Chemistry 351-352-353. Study the chapter summaries from the lecture textbook and your instructor's old sample exams - especially if they contain multiple-choice questions. Review your notes - both PowerPoint notes and the ones you took in class. Work as many of the end-of-chapter problems as you can. If you have taken laboratory courses (Chemistry 354-355), reviewing the material pertaining to specific reactions you did as part of that class may be helpful also. The topics listed below are generally covered in the one-year organic chemistry lecture series. My recommendation is that you use the topic list in conjunction with the textbook and your old exams and notes.

Also keep in mind that you will perform better if you do not leave all the reviewing to the end of the quarter. I suggest that you pick one or two topics to review each week throughout the quarter.

List of Topics to Study

Structure and Bonding
      Lewis structures, molecular orbitals, hybridization
Nomenclature of organic compounds (mostly IUPAC)
Conformations of organic molecules
Stereoisomerism and Chirality
     Fischer projections, cis-trans isomers, E/Z isomers, enantiomers, meso compounds,
     Diastereomers, absolute configuration (R/S), relative configuration (D/L)
Resonance and Electron Delocalization
Acids and Bases
     Strength of acids/bases (pKa), inductive vs. size vs. resonance effects
Addition reactions
     Addition of HX, Markovnikov's rule, halogenation, hydrogenation, oxymercuration and
     Hydroboration of alkenes/alkynes, Diels-Alder reaction
Elimination reactions
     E1 vs. E2, Saytzeff's rule, E1cb elimination, Hofmann elimination
Substitution reactions
     Sn1/Sn2, leaving group ability, nucleophilicity, solvent effects,
     Conversion of alcohols to leaving groups
Carbocation rearrangements
Infrared Spectroscopy (IR)
     Modes of vibration, vibration frequency of common functional groups
Nuclear Magnetic Resonance Spectroscopy (NMR)
     Chemical shift and equivalence, spin-spin splitting
Oxidation and Reduction reactions and reagents
Organometallic reagents
     Alkyllithiums, Grignard reagents, cuprates
Carbonyl chemistry
     Aldehydes and Ketones (preparation, nucleophilic addition to C=O), carboxylic acids
     Acid derivatives and their inter conversions, substitution next to C=O, enolates
     Condensation reactions
Aromatic Substitution Reactions
     Electrophilic aromatic substitution (EAS), activating/deactivating substituents
     Direction effects

How will the standardized exam be figured into my course grade?

Your score will be based on national percentile ranking. A score at the 50th percentile is, by definition, average. Therefore the percentile score must be scaled to reflect grading on a 100-point scale and be consistent with the grade cutoffs listed in the course syllabus.

The class average in organic chemistry is usually 75/100. Therefore, a student scoring at the 50th percentile on the ACS exam should receive a grade of approximately 75%. This scaling will be accomplished by the use of the follwoing formula:

Scaled Score = ACS percentile + [ (100-ACS percentile) (ACS percentile/100) ]

Using the example given above of a student at the 50th percentile on the final, we get:

50 + [ (100 - 50) (50/100) ] = 75

Let's consider some other examples so you can see how this works. The following ACS percentile conversions were calculated using the formula given above:

90 percentile => 99 points, 80 percentile => 96 points, 70 percentile => 91 points,
60 percentile => 84 points, 50 percentile => 75 points, 40 percentile => 64 points,
30 percentile => 51 points, 20 percentile => 36 points, 10 percentile => 19 points.

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