CHM 2211
Test V Checklist
Last updated 11/13/09 2:45 pm

Note: For ease of writing, phrases such as "Be able to", "Know how to", or "You should know" are often omitted from this list of study hints.

Anything from General Chemistry or CHM 2210 (Organic Chemistry I).

Anything from this course (CHM 2211) covered up until now.

Any problems like those assigned from chapters 24 and 25 on topics covered in class since the last test.

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Recognize primary, secondary, or tertiary amines. Recognize a quarternary ammonium salt.

Go back and forth between names and structures for any amine or ammonium salts. Know the names and structures of aniline, pyridine, or pyrrol.

Are asymmetric amines chiral? Optically active? Can their racemic mixtures be resolved? Explain.

Recognize the structural requirements for hydrogen bonding. Which amines are H-bond donors? Acceptors? What are the consequences of H-bonding in amines? B.P., M.P., water-solubility?

Write balanced chemical equations for:

Equilibrium of a given amine reacting in water
Reaction of a given amine with a given acid.

Use pKa of ammoniums to compare relative base strength of various amines.

Order various amines according basicity. Explain the trends

Prepare amines by any of the methods we have discussed in Chapter 24 or earlier. Know the reagents required, the mechanisms if appropriate, and any limitations.

Reduction of nitriles
Reduction of amides
Reduction of aromatic nitro groups
Reduction of azides
Gabriel synthesis
Reductive amination
Hofmann and Curtius rearrangements

Hofmann elimination: What is the reactions sequence? Show each product along the way. What is the observed regiochemistry? Predict the major product.

Show how the reactivity of an arylamine can be attenuated by first converting to an amide. Under what circumstances might this be valuable in a multistep synthesis?

How are arylamines converted to aryldiazonium salts?

Sandmeyer reactions: Show the reagents required or use in multistep synthesis starting with an aryldiazonium to prepare:

Reduced arenes
Aryl halides, ArX where X = Cl, Br, I
Nitriles
Phenols

Show how to make highly-colord compounds via diazonium coupling reactions. Reactants? Limitations?

Spectroscopy of amines: Identify a given amine from it's spectra.

What is the "nitrogen rule" as applied to Mass spectrometry?

What are the expected fragments in the mass spectrum of a given amine? Predict these using the common pattern of alpha cleavage.

What are some characteristic IR signals of amines? How can IR help differentiate between primary, secondary, and tertiary amines?

Describe the expected signals one should expect in the H or 13C NMR spectrum.

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Carbohydrates: Historical and contemporary definitions.

Structures and classifications - know all terms and recognize examples

aldose/ketose
triose/tetrose/pentose/hexose
mono- /di- /tri- /oligo- /polysaccharide

Fischer projections of monosaccharides: conventions, assign D/L, draw, and interpret

Haworth projections: conventions, draw from Fischer projection or vice versa. (McMurry does not use the term "Haworth projection" which refers to the spatially-inaccurate planar representations of cyclic sugars. By convention these are normally drawn with the ring oxygen in the 2 o'clock position for six-membered rings and at the 12 o'clock position for five membered rings.)

Mechanism of hemiacetal formation: reversibility, equilibrium, anomers, anomeric carbon, alpha/beta, pyranose/furanose. (Use or recognize any of these terms.)

Reactions of carbohydrates: Complete partial reactions or use in synthesis:

Exhaustive acylation with acid chloride or anhydride.
Exhaustive methylation with iodomethane and silver oxide.

Glycoside formation (acetal formation): Define, recognize examples between sugars, complete partial reactions, mechanism? Predict hydrolysis products from an oligosaccharide. Name as alpha or beta.

Reduction of monosaccharides with sodium borohydride in water. Complete partial reactions.

Oxidation of monosaccharides: Complete partial reactions for each or use in a multistep synthesis: Bromine in water, Hot nitric acid. Tollens' reagent (contains silver), Benedict's, or Fehling's reagents (contain copper). "Reducing sugars" define or explain. Is fructose a reducing sugar? Explain completely.

Know the structure of glucose.

Name or recognize some specific examples of monosaccharides: glucose, fructose

Name or recognize some specific examples of disaccharides: sucrose, lactose

Name or recognize some specific examples of polysaccharides: starch, cellulose, glycogen

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