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

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

Organic and Biochemical Molecules 2. What is the general formula for a hydrocarbon with one ring and a triple bond? a. CnH2n+2 b. CnH2n c. CnH2n–2 d. CnH2n–4 e. CnH2n–6

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

Organic and Biochemical Molecules 4. Name the following alkanes:

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

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

Organic and Biochemical Molecules 6 . Name the following alkenes.

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

Organic and Biochemical Molecules 8. Name the following alkynes: a. b.

Organic and Biochemical Molecules 9. 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. C6H14 b. C5H10 c. C4H6 d. C4H7Br

Organic and Biochemical Molecules 10. Draw the following molecules. a. para-iodoisobutylbenzene b. meta-tert-butyltoluene c. 2,4,6-tribromophenol

Organic and Biochemical Molecules 11. Write out the reaction for the mono-chlorination of pentane. What type of reaction is this?

Organic and Biochemical Molecules 12. Predict the product for the following addition reactions: a. 1-pentene + Br2  b. 2-butene + HCl  c. 2-pentene + HBr  d. 1-butene + H2O (in the pressence of H+) 

Organic and Biochemical Molecules 13. 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

Organic and Biochemical Molecules 14. Identify the functional groups that are present in the following compounds: aspartame estrogen vanillin

Organic and Biochemical Molecules 15. For each of the following (1) draw the products of oxidation and (2) name the reactants and products:

Organic and Biochemical Molecules 16. Draw the following: a. 4-bromo-3-ethylbutanoic acid b. 6-chloro-3-hexanone c. 2,3-dimethylpentanal

Organic and Biochemical Molecules 17. Classify the following amines as primary, secondary or tertiary; a. tertbutylamine e. ethylhexylamine

Organic and Biochemical Molecules 18. Predict and name the products for the following: a. propanoic acid + 3-methyl-1-butanol  b. methanoic acid + 1-propanol  c. 2,3-dibromohexanoic acid + ethanol 

Organic and Biochemical Molecules 20. What compounds would you use to synthesize the following esters? a. methyl ethanoate b. cyclohexyl propanoate

Organic and Biochemical Molecules 21. Circle the chiral carbons in the following:

Organic and Biochemical Molecules 22. Peptide bonds in proteins are the result of ___________ reactions between __________. Differentiate between primary, secondary and tertiary structures of a protein? How many possible dipeptides will result if you were to mix valine and leucine together?

Organic and Biochemical Molecules 23. Draw gly-phe-ser-ala

Organic and Biochemical Molecules 24. What type of monomers are used to make addition polymers? a. Alkanes b. Alkenes c. Alcohols and carboxylic acids d. Amines and carboxylic acids

Organic and Biochemical Molecules 25. What type of monomers are used to make condensation polymers? a. Alkanes b. Alkenes c. Alcohols and carboxylic acids d. Amines and carboxylic acids

Organic and Biochemical Molecules 26. Draw a short segment of the polymer that is the result of the following monomers: a. tetrafluoroethene b. 4-methyl-2-pentene c. 1,1-dichloro-1-butene

Organic and Biochemical Molecules 27. Draw the monomer used to make the following polymers. a. b. c. d. e.

Organic and Biochemical Molecules 28. Which of the following are examples of condensation polymers? a. Proteins b. DNA c. Polysaccharides d. Polystyrene

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

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

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