Spring 2009 CH302 Worksheet 10 – Organic Chemistry Answer Key 1. How many structural isomers does C4H10 have? Draw them. 2 2. Name them. butane, trimethylmethane 3. How many structural isomers does C7H16 have? Draw them. 9 4. Name them. In order from I-IX: Heptane, 2-Methylhexane, 3-Methylhexane, 2,3-Dimethylpentane, 2,2,3-Trimethylbutane, 3-Ethylpentane. 3,3-Dimethylpentane, 2,2-Dimethylpentane, 2,4-Dimethylpentane H3CCH3H3C CH3CH3H3C CH3CH3CH3IXH3C CH3CH3VIH3C CH3CH3CH3VIIH3CCH3CH3CH3VIIIH3CCH3CH3CH3IVH3CCH3CH3IIIH3CCH3CH3IIH3C CH3IH3CCH3CH3CH3CH3V5. Circle and name the functional groups in these famous compounds. NHONSOCOOHH3CCH3Penicillin GOOHJasmonal - a component of jasmine oilH3CHOCHONorethindrone - active ingredient in Enovid (the first "pill")OH3CHONHOCH3CH3Capsaicin - "heat" causing molecule in chili peppersNHONSOCOOHH3CCH3Penicillin GAromatic ringamideamidecarboxylic acidthiolOOHJasmonal - a component of jasmine oilalkeneketonealdehyde6. Provide the IUPAC name. 3-pentene ethyl ester The three indicates where the alkene starts in the molecule. This is a pentene ester, and the ester contains an ethyl group, making it the ethyl ester H3CHOCHONorethindrone - active ingredient in Enovid (the first "pill")ketonealkenealcoholalkyneorganic trivia:alkenes andketones in this conformationare called "enones".OH3CHONHOCH3CH3Capsaicin - "heat" causing molecule in chili peppersalkeneamideetheralcohol(there is also an aromatic ring, though not highlighted)OO4321OO567. Draw the following: a. 3,3,5-Triethylheptane b. 2-Methylcyclohexanone 8. Draw the following: a. 5,5-Dimethyl-1-hexene b. 2,3,4-trimethyl-4,7-dipropylnonan-1-al c. 5-ethyl- 1,3,6-heptatriene. 9. Name the following. a. CH3CH2CH2CH3 b. CH2(CH2CH3)2 c. CH2(OH)CH2CH2CH2CH(CH2CH3)CH2CH2CH2CH3 CH3OB.H3C CH3H3CCH3CH3A5,5-Dimethyl-1-hexene2,3,4-trimethyl-4,7-dipropylnonan-1-alO5-ethyl-1,3,6-heptatrieneIt helps to draw these out so that you can identify the longest chain and functional groups. 10. Proteins are biological polymers made of amino acids. What type of linkage forms these polymers? Draw the product that would results from these two amino acids reacting together to form a peptide. What type of reaction is this? Remember that these react based on acid/base chemistry. The amine will react with the acid to make an amide bond and release water. H3CCH3a. ButaneCH3H3Cb. Hexane (a CH2 with two ethyl groups hanging off of it.H HH3CCH3c. 5-ethylnonanolHONH2H3COCH3OHOONCH3CH3Alanine methyl ester N,N-dimethylglycineHNH3CO CH3OONCH3CH3Amide linkage formed by an addition reactionof the amine with the carboxylic acid.This amine cannot form an amidelinkage since it has no hydrogens on it.11. What levels of structure organization are possible for proteins and what do these each describe? Primary structure: the amino acid sequence in the peptide chain. Secondary structure: the 3D orientation of these chains (helices and sheets are most common of secondary structures) Teriary structure: Folding that occurs within the protein as sheets and helices adopt lowest energy conformation. Quaternary structure: structure obtained when multiple proteins/ peptides fold and bind to each other. An example of this is hemoglobin which has four separate protein subunits. 12. Draw and name the four DNA bases. 13. Which are the guanines and which are the pyrimidines? 14. What is responsible for the helical structure of DNA? Draw a circle around the H-bonds between base pairs. Hydrogen bonding, refer to below graphic for rest of answer to # 12-14. 15. What is the monomer and formula in the famous polymer that comprises irrigation pipes (PVC, polyvinyl chloride)? Vinyl chloride, CH(Cl)CH2 NNHNNNH2HNNNHNNHNHNNHOH2NNH2OOOCH3Adenine - guanidine baseGuanine - guanidine baseCytosine - pyrimidine baseThymine - pyrimidine baseHClHH16. What types of polymers are there (4 general classes)? Draw examples with A,B notations. Simple polymer- AAAAAAAAAAA Block polymer- AAABBBAAABBBAAA Alternating polymer- ABABABABABA Graft polymer- 17. What is a nucleoside? What is a nucleotide? A nucleotide is a base attached to a sugar (deoxyribose). A nucleotide is a phosphate attached to a nucleoside. 18. What is a fatty acid? What is the difference between saturated and unsaturated? Fatty acids are carboxylic acids with long hydrocarbon chains attached to them. Saturated fatty acids contain only sp3 hydridized carbons in the hydrocarbon chain. As a result, these can pack easily and are usually solid. (think: Crisco). Unsaturated fatty acids contain double bonds. These cause “kinks” in the carbon chains, so they cannot pack as tightly as saturated fats can. (Think: olive oil). 19. What type of reaction is shown below? Elimination, HBr is eliminated from the cyclohexane. 20. What type of reaction generates this ether? Substitution, bromine replaced by methanol. AAAAAAAAAAAA AAAAAAAAAAABBBBBBBBBBBBBBBBBrbaseBrbaseHO
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