Dr. Caroline Sheppard
Chemistry 4401L
Study Guide for Exam
This exam will consist of 40-50 multiple choice or short answer questions. You should bring a calculator and a scantron. Study for this exam by reviewing your graded lab reports and questions, reviewing the experimental procedures and techniques, and considering the following questions:
I. Chemical Literature
● What are some common sources of chemical information? Where would you look to find physical properties? Reactions? Journal reference articles?
● What is a CAS number?
● Be familiar with how to use the following sources: Merck Index; CRC Handbook of Chemistry and Physics; March; Organic Synthesis.
● What are some common abbreviations for journals?
● What are the ACS publications and how do you access them?
II. Diels-Alder Reaction
● What is the Diels-Alder reaction? Be able to draw the products from a reaction (given starting materials), be able to draw the starting materials (given products), and be able to describe the stereochemistry of the reaction.
● Describe the structure of a diene and dienophile.
● How was gas chromatography used in this experiment?
● What was the major constituent of Eucalyptus dives essential oil?
● What was the reaction used in this experiment? Be able to draw starting materials, reagents and products.
● What are some physical properties of the product obtained in this experiment?
● Be able to calculate the theoretical and percent yield of the reaction.
● What did the IR spectroscopy tell you about your compound?
● What would happen if this reaction was run in a wet flask?
● What would happen if the product was heated too long in the recrystallization solvent?
III. Synthesis of PABA Derivatives
● Why should PABA and derivatives of PABA be good UV blockers?
● What is the reaction used in this experiment? What was the starting material? Catalyst?
● What did the UV spectroscopy tell you about your compound?
● What did the IR spectroscopy tell you about your compound?
● Be able to analyze and interpret the NMR spectrum of benzocaine.
● Be able to calculate the theoretical and percent yield of the reaction.
● What is the difference between UVA, UVB, and UVC light?
● Which PABA derivative was predicted to be most efficient at absorbing UV light? Why?
IV. Aldol Reaction
● What is the aldol condensation reaction?
o Be able to draw the products from a reaction (given starting materials) and be able to draw the starting materials (given products).
o What is an enolate? b-Hydroxy carbonyl? a,b-Unsaturated carbonyl?
o What is the best base to use to create an enolate from a neutral carbonyl?
o How does the enolate react with an electrophile? Be able to draw a mechanism.
o What does the product look like if the aldol product is dehydrated? What is the catalyst used in the dehydration step?
● Was the reaction in this experiment a crossed-aldol condensation reaction?
● Be able to draw the products formed from the reaction in this experiment (from any combination of aldehyde and ketone).
● Be able to calculate the theoretical and percent yield of the reactions.
● Why is benzaldehyde a good choice as a starting material for an aldol reaction?
● What would happen to the rate of an aldol reaction if the benzaldehyde starting material was substituted with an electron-donating group?
● What is the Claisen condensation reaction? How is it different from the aldol condensation reaction?
V. Polymers
● What are polymers? What does it mean if a polymer is linear? Branched? Cross-linked?
● What is a copolymer? What are the differences between random, alternating and block copolymers?
● Explain the results of this experiment in terms of the physical and molecular properties of the polymers involved (e.g. cross-linked polymers were stronger, would stretch but not break, etc.)
● What is the polymer used in Styrofoam? Diapers? Glass?
● What are some uses of polyethylene? Poly-vinyl chloride?
● Be able to draw the reaction used to make Nylon-6,6 from adipoyl chloride or adipic acid and 1,6-hexanediamine. What type of reaction is this?
● What is an addition polymer? Condensation polymer?
VI. Food Chemistry
● Describe the chemical components of milk. What are the specific fats, proteins, and carbohydrates that are found in milk?
● What are some food products that can be formed from milk?
● Given the structure of an anomer of lactose, be able to identify the acetal and hemiacetal linkages, and well as whether the structure is the a or b anomer.
● Which anomer of lactose (a or b) is more stable? Why?
● What does the Benedict’s test tell you about a carbohydrate structure?
● How were the proteins and carbohydrates separated from milk?
● What are the plant dyes found in red cabbage?
● Why is red cabbage juice a good acid-base indicator?
VII. Polarimetry
● Be familiar with how to read a Vernier scale
● What is optical rotation? How is it determined? How does the optical rotation for one enantiomer relate to that of the second enantiomer? What types of molecules are optically inactive?
● What is specific rotation? How is it calculated from optical rotation?
● What was the pathlength of the polarimeter cell used in this experiment?
● What was the solvent used in this experiment? How was the solvent adjusted for in the optical rotation calculation?
● What are the structures for (+)-a-pinene and (-)-b-pinene? What is the stereochemistry of each molecule (configurations at the stereocenters)?
● How can the percentage of a component in a mixture be calculated from specific rotation?
● What is a terpene?
VIII. Soaps, Detergents and Dyes
● What is the difference between a soap and a detergent? How do they work?
● What source should be used to make a softer, more soluble soap?
● What happens when chlorosulfonic acid comes into contact with water?
● Be able to draw the reaction for the formation of the detergent in this experiment.
● What is the structure of Para Red? How is it synthesized? Be able to draw this reaction.
● Describe the ingrain, direct, and disperse dying processes. Which type did you use in this experiment?
● Be able to calculate percent recovery and percent yield for the reactions in this experiment.
● What structural features affect the colors of dyes?
IX. Green Chemistry
● What is green chemistry? What are the 12 principles of green chemistry?
● What is an E-factor?
● How is atom economy calculated? How is this used to determine how green a reaction is?
● How is overall reaction yield calculated for a multi-step process?
● What is reaction efficiency? How is it calculated? How is this used to determine how green a reaction is?
● What factors go into determining the safety of solvents?
● What are some things that can be done to make industrial processes greener?
● What are some things that can be done to make the organic chemistry laboratory greener?
● What is a phase-transfer catalyst? How does it work?
General organic lab techniques:
Dr. Caroline Sheppard
Chemistry 4401L
Study Guide for Exam
1. Laboratory safety
2. Melting point determination
3. Liquid-liquid separation using a separatory funnel
4. Vacuum filtration
5. Reflux
6. Distillation
7. Polarimetry
8. Gas chromatography
9. Infrared spectroscopy
10. NMR spectroscopy
11. UV spectroscopy
Dr. Caroline Sheppard
Chemistry 4401L
Study Guide for Exam