AP Chem
Organic Problem Set
1. Propose a synthetic pathway that will transform ethene into:
A. 1.2-dibromoethane
B. Bromoethanol
C. Ethanol
D. Ethyne
E. Ethane
2. Explain why phenol is more acidic than ethanol but less acidic than acetic acid
3. Rank the following compounds from most reactive to least reactive with regards to electrophilic aromatic substitution. For each tell whether the regiochemistry is meta or ortho-para: benzene, chlorobenzene, nitrobenzene, anisole.
4. Draw the structures for cresol and picric acid. Predict which is a stronger acid and tell why.
5. There are three cresols, ortho, meta, and para. Two have identical pKa’s. Predict which two and decide if they are more or less acidic than the other.
6. Which should be a stronger base, aniline or cyclohexylamine? Explain.
7. Most alkanes have a pKa’s around 50. Cyclopentadiene has a pKa of 15. Water is 15.74! Explain why cp is so acidic.
8. Benzene has an octane number of 101 while n-heptane has a value of 0. Explain why this may be and then explain why n-heptane releases more heat per gram when it undergoes combustion.
9. Pyridine is much more basic than pyrrole. Explain.
10. The order for reactivity towards electrophilic aromatic substitution of is pyrrole>furan>thiophene. Explain.
11. Boron trifluoride is less acidic than boron tribromide. Explain.
12. The 1H NMR spectra of propanone, propanal, 1-propanol, and 2-propanol are given below. Decide which is which and rationalize your answers.
13. Identify the molecule whose spectra are shown below:
14. Decide which spectrum goes with which molecule: methyl-tert-butyl ether, ethanol, ethanal, propanone, ethanoic acid, ethyl ethanoate:
15. 1-chloropropane, 2-chloropropane, and chlorobenzene
16. Butan-1-ol, butan-2-ol, and 2-methylpropan-2-ol
17. Draw these functional groups with generic residue groups attached:
A. ester
B. amide
C. alkene
D. alkyne
E. aldehyde
F. ketone
18. Predict the products of these organic reactions:
A. Bromine is added to a generic alkene where trichloromethane (chloroform) is the solvent.
B. Bromine is added to a generic alkene where water is the solvent.
C. HBr is added to a generic alkene.
D. A drop of sulfuric acid is added to a generic alkene dissolved in water.
E. An alcohol is added to concentrated sulfuric or phosphoric acid.
F. A drop of concentrated sulfuric acid is added to a mixture of propanoic acid and ethyl alcohol.
G. A strong base is added to the product from B.
19. The “octane” in gasoline is not octane but 2,2,4-trimethylpentane. Draw this structure.
20. Draw the structures of 1-amino-2-propanol and 1-amino propanone. Assign oxidation states to each atom in each molecule and decide if the conversion from the “ol” to the “one” is an oxidation or a reduction.
21. 1,4-butanediol reacts with a generic diacid to make a diester. Draw Lewis structures for this process.
22. Draw the products of these organic reactions:
A. Bromine is added to a propene where trichloromethane (chloroform) is the solvent.
B. Bromine is added to a butene where water is the solvent.
C. HBr is added to ethene.
D. A drop of sulfuric acid is added to a some alkene dissolved in water.
E. Pentanol is added to concentrated sulfuric or phosphoric acid.
F. A drop of concentrated sulfuric acid is added to a mixture ofeth acid and butyl alcohol.
G. Sodium hydride is added to the product from B.
23. Which is harder, boron trifluoride or borane (boron trihydride)? Are they acids or bases? (10)
24. Insulin is a 51 amino acid protein. It has a unique sequence of amino acids. This sequence is its (2)
A. primary structure B. secondary structure C. tertiary structure D. quaternary structure
25. A certain protein is made when two polypeptides fold up and bind. This coming together of the two structures is the (2)
A. primary structure B. secondary structure C. tertiary structure D. quaternary structure
26. The general three-dimensional form of local segments of biopolymers such as proteins. (2)
A. primary structure B. secondary structure C. tertiary structure D. quaternary structure
27. This amino acid is (5)
A. acidic B. basic
28. Mark the alpha carbon in problem 14. (5)
29. This amino acid is (5)
A. polar B. nonpolar
30. Which amino acid is probably the most basic of these two? (5) (circle one)
31. Which of these amino acids has a redox active side chain that can easily form covalent bonds that are important in protein structure? (5)
32. A segment of protein has many of the amino acid below. It is likely that this segment of the protein is located (5)
A. on the outside of the tertiary structure B. on the inside of the tertiary structure
33. How many amino acids are generally considered proteinogenic? (2)
34. Which type of spectroscopy tells us what fragments a molecule will break into?
A. MS B. IR C. UV-vis D. NMR E. spectrophotometry
35. Which type of spectroscopy can tell the concentration of an unknown?
A. MS B. IR C. UV-vis D. NMR E. spectrophotometry
36. Which type of spectroscopy tells us the types of bonds in a molecule?
A. MS B. IR C. UV-vis D. NMR E. spectrophotometry
37. Which type of spectroscopy would help us identify the difference between these two molecules based on orbitals?
A. MS B. IR C. UV-vis D. NMR E. spectrophotometry
38. A segment of DNA has evolved to be highly resistant to heat. It likely contains more
A. A-T B. G-C
39. The molecule below reacts in a radical reaction with one chlorine molecule. Draw the structure of the product:
40. Which of these molecules is more basic?
41. Which of these molecules is more basic?
42. Which of these molecules is more reactive in radical reactions?
43. Explain your answer to 9.
44. Limonene is a terpene that is responsible for the odor of citrus fruit. Its structure is shown here:
Show the product that is produced in greatest quantity when limonene reacts with HBr.
45. The structure of terpineol is shown here:
What reagent(s) can convert terpineol to limonene?
46. In order to be a good organic reaction, reactions must be selective. Is the reaction you proposed in 3 selective? Why or why not? Selective means that only one product is formed.
47. The structure of eucalyptol is shown here:
Propose a reaction that can break one of the rings.
48. What reagent could convert retinol to retinal?
49. Artemisinin was first described as an antimalarial agent in “The Fifty Two Prescriptions” unearthed from the Mawangdui Han Dynasty tombs. The first modern scientists to learn of this ancient Chinese medicine were skeptical because they believed the molecule was too unstable to be a drug. Why did they think this? Give a good reason based on your knowledge of molecular structure.
Artemisinin:
50. Show the major product when bisabolol reacts with concentrated sulfuric acid.
Bisabolol:
51. Identify the functional groups present in the anabolic steroid testosterone:
52. Which sugar is more active towards oxidation, glyceraldeyde or dihydroxyacetone?
53. Label each as either chitin, cellulose, glycogen, or starch.
54. This is the artificial sweetener aspartame. Split it into two separate amino acids and label the alpha carbons of both amino acids
55.This is the artificial sweetener saccharine. Is the H attached to N more or less acidic than an H in ammonia? Why?
56. P-4000 is an artificial sweetener 4000 times sweeter than sucrose. If P-4000 undergoes electrophilic aromatic substitution, at what site will this occur? Show resonance structures to support your answer.