Frequently Asked Questions about the ACS Standardized Examination in Organic Chemistry

What is the ACS Standardized Exam?

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

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 test, the conditions of the exam are quite specific.  For example:

The serial number of the test booklet you are assigned will be recorded.
All answers must be marked with a No. 2 pencil, and the marks should be very dark.  Any erasures must be complete, leaving no smudges.
You will be provided with scratch paper, but no other reference materials are allowed.  You must turn in all scratch paper at the end of the exam, along with your test booklet and answer sheet.
The exam proctor may not provide any additional information or clarifying statements beyond what is stated in the test booklet.
You may not make any marks on the test booklet!

Are there sample questions available?

YES.  I have assigned Preparing for Your ACS Examination in Organic Chemistry, the Official Guide (published by the ACS Examinations Institute) as a recommended text for Chemistry 353.  In addition, I have been using a selection of multiple-choice questions on many of my examinations during this past year, in an effort to help you become accustomed to this testing format.

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 of 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 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 the laboratory courses (Chemistry 354 and 355), reviewing the material pertaining to specific reactions you did as part of that class may be helpful as well.  The topics listed below are generally covered in the one-year organic chemistry lecture series.  My recommendation is that you the topic list in conjunction with the textbook and your old exams and notes.

Structure and bonding
Lewis structures, molecular orbitals, hybridization
Nomenclature of organic compounds
Conformations of organic molecules
Stereoisomerism and chirality
Fischer projections, cis-trans isomers, E/Z isomers, enantiomers, meso compounds, diastereomers, absolute configuration (R/S)
Resonance and electron delocalization
Acids and bases
Strength of acids/bases (pKa), inductive vs resonance effects, Lewis acid/base theory
Addition reactions
Addition of HX, Markovnikov's rule, halogenation, hydrogenation, oxymercuration, hydroboration of alkenes and alkynes, Diels-Alder reaction.
Elimination reactions
E1 elimination vs. E2 elimination, Saytzeff's rule, E1cb elimination
Substitution reactions
SN1 vs. SN2 substitution, 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, carbon-13 NMR
Oxidation and reduction reactions and reagents
Organometallic reagents
Alkyllithiums, Grignard reagents, dialkylcuprates
Carbonyl chemistry
Aldehydes and ketones (preparation, nucleophilic addition to carbonyl)
Carboxylic acids and derivatives and their interconversion
Substitution next to a carbonyl, enolates, condensation reactions
Aromatic substitution reactions
Electrophilic aromatic substitution, activating/deactivating substituents, directing effects

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

Your score will be based on a national percentile ranking.  A score at the 50th percentile is, by definition, average.  Because the class average in my class is generally somewhat higher than 50%, I must adjust the raw percentile score in order to reflect the grading standards that I use and that I have described in the course syllabus.

The class average on final examinations in organic chemistry is usually around 75%.  Therefore, a student scoring at the 50th percentile on the ACS exam should receive a grade of 75/100 on the final to count toward the course grade.  The challenge, then, is convert this type of analysis to a general equation.  Whatever method of conversion is used, it must be fair, and it must not give an artificially higher boost to students who score at the very top or the very bottom of the percentile rankings.  The conversion method is will be adopted for this course is:

Using this scale factor, a raw score (ACS percentile) of 50 is converted to a 75 final examination percentage.  An ACS percentile score of 70 becomes a 91; an ACS percentile of 30 becomes a 51.