1. Organic and Biochemical Molecules Chapter 21 E-mail: benzene4president@gmail.combenzene4president@gmail.com Web-site: http://clas.sa.ucsb.edu/staff/terri/

2. Organic and Biochemical Molecules 1. Classify the following compounds as saturated or unsaturated.

3. Organic and Biochemical Molecules 2. What is the general formula for a hydrocarbon with one ring and a triple bond?

4. Organic and Biochemical Molecules 3. Draw the following alkanes: a. 4-bromo-3,3-dimethylhexane b. 5-ethyl-2,2,3-trifluoro-3-isopropylheptane c. 3-ethyl-1-methyl-1-propylcyclopentane d. 2-butyl-1-chloro-1-ethylcyclopropane

5. Organic and Biochemical Molecules 4. Name and classify the following. Are any of the molecules chiral?

6. Organic and Biochemical Molecules 5. Draw the following alkenes: a. 4,7-dibromo-3-ethyl-3-methyl-1-heptene b. 3,3-dipropylcyclobutene c. trans-1,3-pentadiene d. cis-2-chloro-5-ethyl-3-octene e. cis-6,7-diethyl-2,3,3-triiodo-4-nonene

7. Organic and Biochemical Molecules 6. Name the following alkenes.

8. Organic and Biochemical Molecules Geometric isomers of alkenes – If each sp2 C has 2 different groups attached it will have two possible orientations due the fact that pi bonds do not allow for free rotation – If each sp2 C has only one hydrogen you can classify the structure as cis or trans Trans 2 Hydrogens are on opposite sides of pi bond Cis 2 Hydrogens are on the same side of pi bond Although these structures are Geometric isomers (the 2 halogens are on opposite sides in the left structure and same side in the right) you don’t refer to them as cis/trans

9. Organic and Biochemical Molecules 6. Draw the following alkynes: a. 3-ethyl-4,5-difluoro-1-pentyne b. 4,4,8-trichloro-7,7-dimethyl-2,5-octadiyne

10. Organic and Biochemical Molecules 7. Name the following alkynes:

11. Organic and Biochemical Molecules 8. For each of the following draw all of the structural isomers. Do any of your structures have geometric isomers? If so, draw and label them. a. C 6 H 14 b. C 5 H 10 c. C 4 H 6 d. C 4 H 7 Br

12. Organic and Biochemical Molecules 9. Molecules with benzene are classified as_________. (circle all that apply) a. Alkanes b. Alkenes c. Alkynes d. Aromatic e. Saturated f. Unsaturated

13. Organic and Biochemical Molecules 10. Draw the following molecules. a. para-iodoisobutylbenzene b. 1-tert-butyl-4-chloro-2-ethylbenzene c. 2,4,6-trinitrotoluene

14. Organic and Biochemical Molecules 11. Identify the functional groups that are present in the following compounds: aspartameestrogen caffeine vanillin cocaine

15. Organic and Biochemical Molecules 12. Name and classify the following:

16. Organic and Biochemical Molecules 13. Draw the following: a. 3-isopropyl-2,4,6-heptanetriol b. dibutyl ether c. isopropyl methyl ether d. tertbutylamine e. ethyldimethylamine

17. Organic and Biochemical Molecules 14. Name and classify the following:

18. Organic and Biochemical Molecules 15. Name and classify the following:

19. Organic and Biochemical Molecules 16. Name and classify the following:

20. Organic and Biochemical Molecules 17. Name and classify the following:

21. Organic and Biochemical Molecules 18. Write out the reaction when propane and chlorine are mixed in the presence of UV light. What type of reaction is this?

22. Organic and Biochemical Molecules 19. Predict the product for the following addition reactions: a. 1-pentene + Br 2  b. 2-butene + HCl  c. 2-pentene + HBr  d. 1-butene + H 2 O (in the pressence of H + ) 

23. Organic and Biochemical Molecules 20. Which of the following transitions does not represent a hydrogenation reaction? a. 1-butene  butane b. 1-pentyne  pentane c. pentane  2-pentene d. butanal  1-butanol

24. Organic and Biochemical Molecules 21. Single oxidation of primary alcohols result in _________ whereas double oxidation of primary alcohols result in __________. Secondary alcohols can only be oxidized once to produce ________. Tertiary alcohols in the presence of an oxidant results in ________.

25. Organic and Biochemical Molecules 22. Write out the reactions for oxidation of the following compounds. Name the products. a. 3-bromocyclopentanol b. 3,4-dimethyl-1-hexanol c. 2,2-dimethyl-3-heptanol d. 1-methylcyclobutanol e. phenol f. 3,3,3-trichloro-1-propanol

26. Organic and Biochemical Molecules 23. Esters are the result of a _________ reaction between _______ and _______ in the presence of ________.

27. Organic and Biochemical Molecules 24. Predict and name the products for the following: a. propanoic acid + 1-butanol  b. methanoic acid + 1-propanol  c. hexanoic acid + ethanol 

28. Organic and Biochemical Molecules 25. What compounds would you use to synthesize the following esters? a. methyl ethanoate b. cyclohexyl propanoate

29. Organic and Biochemical Molecules 26. Circle the chiral carbons in the following: glucose testosterone

30. Organic and Biochemical Molecules 27. Peptide bonds in proteins are the result of ___________ reactions between ____________. How many possible dipeptides will result if you were to mix valine and leucine together? Valine Leucine

31. Organic and Biochemical Molecules 28. Draw gly-phe-ser-ala Glycine Phenylalanine Serine Alanine

32. Organic and Biochemical Molecules 29. What type of monomers are used to make addition polymer? a. Alkanes b. Alkenes c. Alkynes d. Alcohols and carboxylic acids

33. Organic and Biochemical Molecules 30. The monomer used to make teflon is tetrafluoroethene. Draw a short segment of teflon.

34. Organic and Biochemical Molecules 31. Draw the monomer used to make the following polymers. a. b. c. d. e.

35. Organic and Biochemical Molecules 35. Which of the following are examples of condensation polymers? a. Proteins b. DNA c. Polysaccharides d. Polystyrene

36. Organic and Biochemical Molecules 1. Saturated => all single bonds Unsaturated => double or triple bonds 2. 3. a. 4-isopropyl-5-methyloctane b. 2,5,5-trichloror-4-propylheptane c. 2-bromo-4-isobutyl-1-methylcyclohexane

37. Organic and Biochemical Molecules 4. 5. a. 4-fluoro-5-methyl-3-heptane b. 3-chloro-1isopropylcyclohexene c. cis-2-hexane d. trans-8,8-dibromo-4-methyl-2-octene e. 5,8-diethyl-1,7-decadiene

38. Organic and Biochemical Molecules 6. 7.

39. Organic and Biochemical Molecules