Assignment 2 –complete – Due March 28, 2007
1. Show all the steps with appropriate reagents for the following transformations.
Cl
O
O
OH
OH
O
CH3O
O
H
O
CH3CH2OCCH3
O
CH3CH2COCH3
O
O
2. Predict the product. Show all the intermediates.
OCH3
O
cat. HCl
NH2
O
NH2
1. LDA
2.
Br
O
CO2CH3
Br
3. H3O , MeOH, anhydrous
4. LiAlH4 , Et2O
5. H3O , r.t., 2 h
O
O
CH3
O
1. Ph3PCH
O
TBDMS O
2. NaOH, H2O, heat
CHO
CH3CO2H
3. H3O, H2O, 50° C, 3 hrs
1) SO2Cl, py
2) AlCl3, C6H6
3) NaOEt, EtOH
3. Crossword puzzle.
Across
1. First thing you should do when approaching a multistep synthesis.
5. Common thermoplastic polymer
7. Organic acid
9. Condensation reaction spelled backwards
11. Two-carbon olefin
13. Tautomer in equilibrium with enol tautometer
15. Spectroscopy for studying conjugated molecules
16. Common high boiling aprotic solvent
17. Compound with opposite charges on adjacent carbons
18. Prefix for a carbon bonded to three other carbons
20. Silicon symbol
21. Congratulatory drink raised high after passing organic chemistry
23. Reduction product of a carbonyl compound with sodium borohydride
25. Glass transition temperature
26. Intermediate in reaction that cleaves a double bond
28. Answer given by Professor Georges when asked if the final organic chemistry exam
will be overly tough
29. Class average in CHM243 mid-term test
30. Rate constant for alkoxyamine decomposition
OH
32.
33. Truculent organic chemistry professor
35. Excellent leaving group derived from an alcohol
36. Stereochemistry
Br
H
H
OH
37. Reduces esters at low temperatures to aldehydes
39. Antimony symbol
41. Cooking measurement not used in organic chemistry
42. Converts immediately to a ketone
44. Boat conformation for cyclohexane
46. Osmium symbol
47. Weighing --49. Nine-carbon alkane
52. Titanium symbol
53. Protein that transports lipids through the body
54. An article
55. Describes the speed of a reaction
58. Diet for celiac
59. Conjugated olefins
60. Region of electromagnetic spectrum from 7.8 x 10-7 m to 10-4m
61. organic --Down
2. Type of alcohol
OH
3. O3
4. Protecting group for alcohols
5. Precursor for making alcohols
6. Transition ----7. Intermediate from reaction of 25% H2SO4 with a tertiary alcohol at 50C
8. How a student often fells after writing an organic chemistry test
10. Reaction accomplished with NaBH4, LiAlH4, H2 Pd/C
12. Titanium symbol
13. Functional group that generally can not be oxidized any further
14. Mercuration
19. Reaction for converting aldehyde to acid
20. First reaction in preparation of Wittig reagent
22. Prefix for one of the products of the Wittig reaction
23. Serious disease infecting millions of people
24. Molecular orbital
27. Nuclear overhauser effect
30. Protecting group for a carbonyl group
31. Reaction to make olefins
33. Conformation
34. Building block for nucleic acid
36. Addition to the same side of a double bond
37. Degree of polymerization
38. 12C, 13C
40. Aromatic, single ring
42. ,-unsaturated carbonyl compound
43. Analgesic
45. Supervises undergraduate lab
48. “That is --- an option”
50. Instrument that enables the study of the position of hydrogens in a molecule
51. Byproduct of sodium hydroxide with an acid chloride
53. Pair of electrons on the nitrogen of an amine
56. Professor Georges considers his exams a work of --57. ---ball