Abbreviations/ General Info
Labs 1-3
Labs 4,5
Labs 6,7
NMR
100
NMR; IR; MeOH; TLC; Rf (both names).
Nuclear Magnetic Spectroscopy; Infra Red; Methanol; Thin Layer Chormatography; Retention/Retardation Factor.
100
Why did you flame dry the apparatus in Lab 2 (Diels-Alder) and Lab 3 (Friedel Krafts)?
Diels - cross product. Friedels - Lewis Acid decomposition.
100
Draw the following structures: a.) Benzhydrol b.) Benzaldehyde. c.) Tosylate side-chain.
Page 113.
100
Is the Ether Synthesis performed on methyl diantilis precursor an Sn1 or Sn2? EXPLAIN your reasoning using principles of electrons, charge etc.
Pg 119; personal discretion.
100
a.) What is the NMR reference compound? Structure? why? explain. b.) What is the NMR solvent? Structure? Why? c.) Degrees of Unsaturation. d.) Name five elements that can be studied using NMR.
a.) TMS deshielded.(pg 150 @ back) b.) CDCl3 (NMR solvent) (pg 150 @ back) c.) C'mon.Seriously. d.) H,C,N,P,F (149).
200
Name all the equipment for a reflux apparatus and their position in the apparatus.
Page 65
200
List and describe in detail the two uses of the TLC process.
Page 86.
200
Draw the structure of lithium aluminum hydride, sodium borohydride, 3-ethoxy-4-hydroxybenzaldehyde.
Page 116,117.
200
Name three drying agents. Which one interferes with the drying of amines and why?
Na2So4; CaCl2; MgSo4. (Page 48)
200
What are the four categories that give us information from an NMR spectrum? Explain each category in brief detail.
Page 86.
300
List sequential steps in preparing an unknown sample for IR spectroscopy.
Page 83
300
DIELS ALDERS PRACTICE http://classes.uleth.ca/200801/chem2600a/practice_questions.html#da (EXERCISE 84 - solve any 2 from products and reactants)
http://classes.uleth.ca/200801/chem2600a/practice_questions.html#da
300
a.)What was the gas that was evolved during the synthesis of Methyl Diantilis precursor? b.)What acid was used? Why was it added slowly? c.)Could you use Sulfuric Acid? What differences would you see in observations? c.) Why was the original compound dissolved in base?
a.) hydrogen. b.) HCl. lots of reasons: experimental conditions, acidic environment could protinate. c.) Yes, faster time and more bubbles. b.) Deprotinate all.
300
What is Green Chemistry? Why does the Aldol Condensation reaction you did qualify under Green Chem.?
Page 121; lose water no other chemicals.
300
(State the number of chemically non-equivalent hydrogen in the pale yellow and orange)? http://www.wissensdrang.com/media/wis1l.gif
(Orange) - 15. (Yellow) - 8. (16 - you didnt account for symmetry) Discuss integration? BONUS.
400
What causes an emulsion? Name at least 3 ways to "break" an emulsion (6 in total) (bonus ways gives you bonus marks)
Page 64
400
Answer these three questions (in any order): a.) A reaction between a benzene ring and an appropriate electrophilic carbocation will result in _____? What happens to the charge? b.) What is hygroscopic? Based on this principle state the use of Silica Gel in packaging and also explain the reason you should not eat it. (FREEBIE) c.) What is a drawback of Friedel-Krafts Alkylation? Why did this not happen in your experiment?
a.) intermediate carbocation. resonates. b.) absorbs atmospheric moisture; dessicant - Silica Gel : constant state of dryness since moisture may spoil said thing; dry up and moreover poisonous. c.) Further alkylation; you used a tertiary.
400
a.) Why do we need to dry glassware when making a Benadryl precursor in Lab 4. b.) Show the reaction scheme (with intermediates) for a Grignard reagants that is reacting with oxygen. c.) Show the reaction scheme for Wurtz Coupling.
Page 111
400
MATCH THESE pKa values to appropriate class of compounds: 24,3.77,15.5,4.76,46,-10, 19.3,2.9. - acetone, cyclopropane, methanoic acid, hydroiodic acid, chloroethanoic acid, methanol, acetic acid, ethyne.
acetone (19.3), cyclopropane (46) , methanoic acid (3.77), hydroiodic acid (-10), chloroethanoic acid (2.9), methanol (15.5), acetic acid (4.76), ethyne (24).
400
PREVIOUS LINK. How would the NMR and IR of yellow differ from red-purple.
DISCUSS
500
You have a compound that has a very similar structure to benzaldehyde. List ALL the steps required for isolation via a two step recrystallization process and proper identification methods. LIST ALL POSSIBLE methods.
Page 39,46,49,53,73,78, supplementary NMR.
500
Give the proper mechanism and all products for the following reactions: a.) Friedel-Crafts Alkylation. b.) Diels-Alder reaction of 1,3-butadiene and maleic anhydride. c.) Friedel-Crafts Acylation.
Page 104 + lectures. You should know these very well.
500
Show the following MECHANISMS: a.) FULL Grignard reaction to produce a carboxylic acid, tertiary alcohol (start with ETHENE) b.) Give the mechanism of reaction of LiAlH4 with a generic ester, carboxylic acid and ketone.
a.) Page 112, b.) 115/116.
500
Okay, so pay attention: a.) What is one major condition for aldol condesation for the environment. b.) What is one major condition for the reactant structure. c.) Show the entire mechanism with arrows and products for the production of tetraphenylcyclonepentadienone.
a.) base. b.) alpha-H c.) KNOW THIS. KNOW KNOW KNOW THIS!
500
Sketch a somewhat accurate splitting pattern of sinapic acid. ALSO sketch its major peaks of the IR spectrum (approx) http://ars.els-cdn.com/content/image/1-s2.0-S0308814607000386-gr1.jpg
DISCUSS.
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