Organic and Biochemical MoleculesChapter 21E-mail: benzene4president@gmail.comWeb-site: http://clas.sa.ucsb.edu/staff/terri/

Organic and Biochemical Molecules1. Classify the following compounds as saturated or unsaturated.

Organic and Biochemical Molecules2. 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 Molecules3. Draw the following alkanes:

a. 4-bromo-3,3-dimethylhexaneb. 3-ethyl-1-methyl-1-propylcyclopentanec. 5-ethyl-2,2-difluoro-3-isopropylheptaned. 4-sec-butyl-1-chloro-1-ethylcyclohexane

Organic and Biochemical Molecules4. Name and classify the following. Are any of the molecules chiral?

Br

Cl

Cl

Organic and Biochemical Molecules5. Draw the following alkenes:

a. 4,7-dibromo-3-propyl-2-hepteneb. 3,3-dipropylcyclobutenec. trans-1,3-pentadiened. cis-2-chloro-5-ethyl-3-octene

Organic and Biochemical MoleculesGeometric 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

H

H HH

Trans2 Hydrogens are on

opposite sides of pi bond

Cis2 Hydrogens are on

the same side of pi bond

F

Cl FCl

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 Molecules6 . Name the following alkenes.

Organic and Biochemical Molecules7. Draw the following alkynes:

a. 3-ethyl-4,5-difluoro-1-pentyneb. 7,7-dimethyl-2,4-octadiyne

Organic and Biochemical Molecules8. Name the following alkynes:

a.

b.

Organic and Biochemical Molecules9. 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 Molecules10. Draw the following molecules.

a. para-iodoisobutylbenzene b. meta-tert-butyltoluenec. 2,4,6-tribromophenol

Organic and Biochemical Molecules11. Write out the reaction for the mono-chlorination of pentane. What

type of reaction is this?

Organic and Biochemical Molecules12. 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 Molecules13. Which of the following transitions does not represent a

hydrogenation reaction?a. 1-butene butaneb. 1-pentyne pentanec. pentane 2-pentened. butanal 1-butanol

Organic and Biochemical Molecules14. Identify the functional groups that are present in the following

compounds:

aspartame estrogen vanillin

Organic and Biochemical Molecules15. For each of the following (1) draw the products of oxidation and (2) name the reactants and products:

Organic and Biochemical Molecules16. Draw the following:

a. 4-bromo-3-ethylbutanoic acidb. 6-chloro-3-hexanonec. 2,3-dimethylpentanal

Organic and Biochemical Molecules17. Classify the following amines as primary, secondary or

tertiary;a. tertbutylaminee. ethylhexylamine

Organic and Biochemical Molecules18. 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 Molecules20. What compounds would you use to synthesize the following esters?

a. methyl ethanoateb. cyclohexyl propanoate

Organic and Biochemical Molecules

OH

O

H OHH OHH OH

21. Circle the chiral carbons in the following:

Organic and Biochemical Molecules22. 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 Molecules23. Draw gly-phe-ser-ala

Organic and Biochemical Molecules24. What type of monomers are used to make addition polymers?

a. Alkanesb. Alkenesc. Alcohols and carboxylic acidsd. Amines and carboxylic acids

Organic and Biochemical Molecules25. What type of monomers are used to make condensation

polymers?a. Alkanesb. Alkenesc. Alcohols and carboxylic acidsd. Amines and carboxylic acids

Organic and Biochemical Molecules26. Draw a short segment of the polymer that is the result of the

following monomers:a. tetrafluoroetheneb. 4-methyl-2-pentenec. 1,1-dichloro-1-butene

Organic and Biochemical Molecules27. Draw the monomer used to make the following polymers.

a.

b.

c.

d.

e.

Organic and Biochemical Molecules28. Which of the following are examples of condensation polymers?

a. Proteinsb. DNAc. Polysaccharidesd. Polystyrene

Organic and Biochemical Molecules1. Saturated => all single bonds Unsaturated => double or triple bonds2.

3. a. 4-isopropyl-5-methyloctane b. 2,5,5-trichloror-4-propylheptane c. 2-bromo-4-isobutyl-1-methylcyclohexane

Organic and Biochemical Molecules4.

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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7.

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