CHM 235IN Final Exam Topics
Background material 36%
1. Describe the hybridization schemes for carbon in organic molecules
2. Write organic molecules using skeletal shorthand
3. Predict whether a molecule is polar or non-polar
4. Identify common functional groups in organic molecules
5. Name an alkane, alkene, alkyne, or alkyl halide given a formula, including stereochemistry
6. Draw a Newman projection for an alkane
7. Differentiate axial from equatorial positions in chair cyclohexane
8. Recognize torsional, steric, and ring/angle strain in a molecule
9. Recognize a chiral center in an organic molecule
10. Name enantiomers using R and S nomenclature
11. Recognize enantiomers, diastereomers, and meso compounds in molecules with two chiral centers
12. Describe the formation of a racemic mixtures of enantiomers
Organic Reactions 48%
13. Define an addition, elimination, substitution, and rearrangement reaction
14. Distinguish between heterolytic and homolytic bond cleavage
15. Write the mechanism for an electrophilic addition reaction
16. Use Markovnikov’ s rule to predict the product of an electrophilic addition
17. Recognize a carbocation rearrangement via hydride or methyl shift
18. Draw the mechanism for a reaction occurring under SN1, SN2, E1, or E2 conditions
19. Predict product stereochemistry for SN1, SN2, E1, or E2 reactions
20. Describe how nucleophile/base, substrate, leaving group, and solvent affect SN1, SN2, E1, or E2 reactions
21. Predict the major organic product(s), including stereochemistry, for the following organic reactions:
1. a) Preparation of alkyl halides via radical halogenation of alkanes
2. b) Preparation of an alkene via dehydrohalogenation of an alkyl halide
3. c) Preparation of an alkene via dehydration of an alcohol
4. d) Formation of a dihalide via addition of a halogen to an alkene
5. e) Formation of a halohydrin via addition of a halogen to an alkene
6. f) Formation of an alcohol via addition of water to an alkene
7. g) Formation of an alcohol via oxymercuration of an alkene
8. h) Formation of an alcohol via hydroboration of an alkene
9. i) Formation of cyclopropane via addition of a carbene to an alkene
10. j) Formation of an alkane via addition of hydrogen to an alkene
11. k) Formation of a trans-diol via formation and hydroxylation of an epoxide
12. l) Formation of a cis-diol via oxidation of an alkene with OsO4
13. m) Formation of an aldehyde or ketone via ozonolysis of an alkene
14. n) Formation of a carboxylic acid via oxidation of an
