OAT (Optometry Admission Test) Organic Chemistry Syllabus

Organic Chemistry syllabus — full chapter and topic list

Expand any chapter to see its topics and sub-topics. This is the whole examinable outline for Organic Chemistry in OAT (Optometry Admission Test), not a summary of it.

1. 1

   Structure, Bonding, and Nomenclature

   3 topics

   • Bonding and Hybridization
     • Sigma and pi bonds
     • sp, sp2, sp3 hybridization
     • Resonance
   • IUPAC Nomenclature
     • Naming alkanes, alkenes, and alkynes
     • Naming functional groups
   • Functional Group Identification
     • Recognizing major functional groups
     • Acidity and basicity of organic compounds
2. 2

   Stereochemistry

   3 topics

   • Isomerism
     • Structural and constitutional isomers
     • Conformational analysis
   • Chirality
     • Enantiomers and diastereomers
     • R/S configuration
     • Optical activity and meso compounds
   • Stereochemistry in Reactions
     • Retention and inversion of configuration
     • Racemization
3. 3

   Reaction Mechanisms

   4 topics

   • Substitution Reactions
     • SN1 and SN2 mechanisms
     • Nucleophiles and leaving groups
   • Elimination Reactions
     • E1 and E2 mechanisms
     • Zaitsev and Hofmann products
   • Addition Reactions
     • Electrophilic addition to alkenes
     • Markovnikov's rule
   • Reaction Intermediates
     • Carbocations, carbanions, and radicals
     • Stability and rearrangements
4. 4

   Reactions of Functional Groups

   4 topics

   • Alcohols, Ethers, and Epoxides
     • Oxidation and dehydration
     • Epoxide ring opening
   • Carbonyl Chemistry
     • Aldehydes and ketones
     • Nucleophilic addition
     • Carboxylic acids and derivatives
   • Aromatic Compounds
     • Aromaticity and Huckel's rule
     • Electrophilic aromatic substitution
   • Amines
     • Basicity and reactions of amines
5. 5

   Spectroscopy and Lab Techniques

   3 topics

   • Spectroscopy
     • IR spectroscopy
     • NMR spectroscopy
     • Mass spectrometry and UV-Vis
   • Separation and Purification
     • Extraction and distillation
     • Chromatography and recrystallization
   • Synthesis and Reaction Design
     • Multistep synthesis and retrosynthesis
     • Predicting products and reagents

Organic Chemistry flashcards for OAT (Optometry Admission Test)

25 of 51 cards from the Organic Chemistry deck — real questions with worked answers.

1. In carbon hybridization, how do sp, sp2, and sp3 hybridized carbons differ in geometry and bond angle?

   sp: linear, 180 degrees (2 sigma + 2 pi possible); sp2: trigonal planar, 120 degrees (3 sigma + 1 pi); sp3: tetrahedral, 109.5 degrees (4 sigma bonds).

2. How does s-character affect bond length, bond strength, and acidity of a C-H bond?

   Greater s-character (sp > sp2 > sp3) means shorter, stronger bonds and a more acidic, more electronegative carbon, so terminal alkyne C-H is the most acidic.

3. What is the difference between a sigma bond and a pi bond?

   A sigma bond forms by head-on orbital overlap and allows free rotation; a pi bond forms by side-on p-orbital overlap, is weaker, and restricts rotation.

4. How many sigma and pi bonds are in a triple bond, and how does this relate to hybridization?

   A triple bond has 1 sigma + 2 pi bonds; the atoms are sp hybridized.

5. What does degree of unsaturation (index of hydrogen deficiency) tell you, and what is its formula for CnHmNpOq?

   It counts rings plus pi bonds. Degrees = (2C + 2 + N - H)/2 (oxygen is ignored; each halogen counts like an H).

6. In IUPAC nomenclature, what is the order of priority for selecting the principal characteristic group (highest to lower)?

   Carboxylic acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > ether (alkene/alkyne and halogens are treated as substituents/lower).

7. What suffix and prefix are used to name a ketone versus an aldehyde in IUPAC nomenclature?

   Aldehyde: suffix -al (prefix oxo- or formyl-); Ketone: suffix -one (prefix oxo-). Aldehyde carbon is always C1.

8. How are E and Z descriptors assigned to a double bond?

   Use CIP priorities on each carbon: Z (zusammen) = higher-priority groups on the same side; E (entgegen) = on opposite sides.

9. How do you assign R or S configuration to a chiral center?

   Rank the four groups by CIP priority (highest atomic number first), point the lowest-priority group away, and trace 1->2->3: clockwise = R, counterclockwise = S.

10. What is the IUPAC name format for a compound with both a hydroxyl and a higher-priority carboxylic acid group?

    The acid is the suffix (-oic acid) and the OH becomes the hydroxy- prefix, e.g., 3-hydroxybutanoic acid.

11. What functional group has the structure R-CO-O-CO-R, and what is it called?

    An acid anhydride (two acyl groups joined by an oxygen).

12. How can you distinguish an ether, an ester, and an alcohol by functional group structure?

    Alcohol: C-OH; Ether: C-O-C (no carbonyl); Ester: C(=O)-O-C (carbonyl plus single-bonded O).

13. What is the functional group of a nitrile, and what is its hybridization?

    A nitrile is C(triple bond)N; the carbon and nitrogen are sp hybridized, giving a linear arrangement.

14. What is the difference between constitutional (structural) isomers and stereoisomers?

    Constitutional isomers have the same molecular formula but different connectivity; stereoisomers have the same connectivity but differ in spatial arrangement.

15. What is the difference between enantiomers and diastereomers?

    Enantiomers are non-superimposable mirror images (all stereocenters opposite); diastereomers are stereoisomers that are not mirror images (some but not all stereocenters differ).

16. What defines a meso compound?

    A molecule containing stereocenters but possessing an internal plane of symmetry, making it achiral (optically inactive) despite having chiral centers.

17. What is the maximum number of stereoisomers for a molecule with n stereocenters, and when is it fewer?

    Maximum is 2^n; it is fewer when meso compounds exist due to internal symmetry.

18. What is the difference between conformational isomers and configurational isomers?

    Conformers interconvert by rotation about single bonds (no bond breaking), e.g., chair/boat; configurational isomers require breaking bonds to interconvert.

19. What is a chiral center (stereocenter)?

    An atom (usually carbon) bonded to four different groups, producing a non-superimposable mirror image.

20. What does a racemic mixture (racemate) consist of, and what is its optical rotation?

    A 50:50 mixture of two enantiomers; its net optical rotation is zero because the rotations cancel.

21. What is the relationship between specific rotation and enantiomeric excess?

    Observed rotation reflects ee; %ee = (observed rotation / rotation of pure enantiomer) x 100, and also equals %major - %minor enantiomer.

22. In an SN2 reaction, what happens to the stereochemistry at the reacting carbon?

    Inversion of configuration (Walden inversion) because the nucleophile attacks the backside opposite the leaving group.

23. What stereochemical outcome results from an SN1 reaction at a chiral center?

    Racemization (a mix of retention and inversion) because the planar carbocation intermediate is attacked from both faces.

24. Compare SN1 and SN2 in terms of kinetics, substrate preference, and nucleophile strength.

    SN1: first-order, favors 3 degree substrates, weak nucleophile/polar protic solvent, carbocation intermediate. SN2: second-order, favors methyl/1 degree, strong nucleophile/polar aprotic solvent, concerted.

25. How does leaving group ability trend, and why?

    Better leaving groups are weaker bases (more stable anions): I- > Br- > Cl- > F-, and tosylate/triflate are excellent; OH-, NH2-, and R-O- are poor leaving groups.

See more Organic Chemistry flashcards →

Planning Organic Chemistry for OAT (Optometry Admission Test)

Organic Chemistry (OAT (Optometry Admission Test)) FAQ