CH 102 Review worksheet

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102

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Chemistry

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Jan 9, 2024

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CH 102 Review worksheet 1. Of the following molecules, indicate, i.e., give the letter, which represent structural isomers [___________________] and which are identical molecules [_____________________]. (a) (b) (c) (d) (e) (f) 2. Under each molecule, give the IUPAC name for the following molecules (a) (b)
(c) (d) 3. Draw the line structural formula for each of the following: a. 2,2,4-trimethylhexane b. 2,2-dimethylpropane c. 3-ethyl-2,4,5-trimethyloctane d. 4-isoproplyoctane e. 2,3-dichloropentane f. 1-chloro-4-methylcyclohexane 4. One of the few reactions that alkanes undergo is combustion. Give the equation that describes the combustion of hexane. 5. Write the IUPAC names for, isopentane CH 3 CH(CH 3 )CH 2 CH 3 , neopentane C(CH 3 ) 4 , and tertiary butane.
6. Draw the structures of the molecules below, and explain why each of the following is an incorrect name for the molecule. Give the correct name. a. 1,3-dimethylbutane b. 4-ethylpentane c. 2,2-diethylpropane d. 2-ethyl-3-methylpentane e. 2-propylpentane f. 2,2-diethylheptane g. 5-ethyl-1-methylcyclohexane 7. Draw a structural formula for at least one bromoalkene with the molecular formula C 5 H 9 Br that (a) shows cis-trans isomerism (one structure) and (b) one that does not show cis-trans isomerism (one structure).
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8. The IUPAC name of an alkene is derived from the name of the longest carbon chain that contains the carbon-carbon double bond. a. True b. False 9. The IUPAC name of CH 3 CH=CHCH 3 is 1.2-dimethylethene. a. True b. False 10. 2-methyl-2-butene shows cis-trans isomerism. a. True b. False 11. The IUPAC name of CH 2 =CHCH=CHCH 3 is 1,3-pentadiene. a. true b. false 12. 1,3-butadiene has two carbon-carbon double bonds and so has 2 2 = 4 possible stereoisomers a. true b. false 13. Draw a structural formula for each of the following a. 3-chloropropene b. 3-methylcyclohexene c. 1,2-dimethylcyclohexene d. trans-3,4-dimethyl-3-heptene
e. 3-hexyne f. p-chloroaniline g. 1,3-dimethylbenzene h. 2-isopropyl-5-methylphenol i. benzoic acid (you’ll have to look this one up!) j. toluene 14. Name the following molecules: a. b.
c. d. e. f. g. 15. In your own words, explain why benzene is not cyclohexatriene, and what is meant by resonance. 16. Draw and label the cis- and trans- isomers of 2-butene. 17. Draw the product(s) from the following reactions. 4- methylcyclohexene + H 2
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Pt 2-butene + H 2 O H2SO4 1,3-butadiene + excess Br 2 ethene + HBr 18. Draw a structural formula for an alkene with the molecular formula C 5 H 10 that reacts with HCl to give the indicated chloroalkane as the major product. 19. Relative to alkanes and alkenes, an alcohol of similar molar mass will a. have a higher boiling point b. have a lower boiling point c. have a similar boiling point d. more detail is needed to know 20. The reaction alcohols undergo in which water is eliminated is called a. hydration b. hydrogenation c. dehydration d. moisturizing
21. The oxidation of a primary alcohol yields a. an alkene b. a ketone c. an aldehyde d. an alkane 22. The oxidation of a secondary alcohol yields a. an alkene b. a ketone c. an aldehyde d. an alkane 23. In an ether such as CH 3 OCH 3 , the C-O-C angle is a. 180 b. ~90 c. ~109 d. ~120 24. Compared to alcohols, ethers are a. more reactive b. less reactivec. they have similar reactivities 25. Comparing ethanol and butanol, which would you expect to be more soluble in water? a. ethanol b. butanol c. they will have similar solubilities d. they are both insoluble in water 26. A name for CH 3 CH 2 CH 2 SH is a. propane thiol b. propylhydrogensulfide c. propylthioether 27. 2 points) What physical properties, e.g., boiling point, vapor pressure, viscosity, distinguish an alcohol from an ether? Explain why the physical properties are so different. 28. (2 points) Give a clear explanation for why alcohols are far more soluble in water than alkanes. 29. (1 point each) Draw structures below each of the following seven molecules 3-methyl-1-pentanol
1,2-pentanediol 4-chloro-2-butanol Butylethyl ether 2-methoxy-1-ethanol m-chlorophenol ethyl mercaptan 30. (2 points) Draw all possible structural isomers with the formula C 4 H 10 O. 31. (1 point each) Name the following molecules.
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32. (2 points each) What alkene (and other reagents) would you use as a starting material to make the following alcohols? Hint : remember Markovnikov’s Rule. 33. (2 points each) Starting from cylcohexanol, show how you would prepare Cyclohexanone Cyclohexene Bromocyclohexane 34. (2 points each) Give the product formed in the following reactions: [O]
Ethanol Cyclopentanol Tertiary-butyl alcohol 2-cyclohexen-ol 3-methyl-2-pentanol 35. (1 pt)What is the fundamental functional group of aldehydes, ketones, and carboxylic acids? 36. (1 pt) Give a general route for the synthesis of an aldehyde. 37. (1 pt) Give a general route for the synthesis of a ketone 38. (1 pt) Give a general route for the synthesis of a carboxylic acid 39. ( ½ pt each) Draw structural formulas for the following aldehydes: Formaldehyde 3,7-dimethyloctanal [O] [O] [O] [O]
2,3-dihydroxypropanal benzaldehyde 40. ( ½ pt each) Draw structural formulas for the following ketones Ethylisopropyl ketone 2-chlorocyclohexanone 2,4-dimethyl-3-pentanone acetone 41. ( ½ pt each) Draw structural formulas for the following carboxylic acids Dichloroacetic acid 4-phenylbutanoic acid cis -3-hexenedioic acid 3,5-dimethylbenzoic acid 42. ( ½ pt each) Draw structural formulas for the following carboxylates potassium benzoate calcium propanoate
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Ethyl acetate isopropyl propanoate 43. (1 pt each) Name the organic reactant, give the product, and name the organic product in each of the following reactions: Cr 2 O 7 -2 /H 2 SO 4 Cr 2 O 7 -2 /H 2 SO 4 + NaOH(aq) + Ca(OH) 2 (aq)
+ CH 3 CH 2 OH 44. (1 pts) Aldehydes are often stored under nitrogen rather than in air. Give a good reason for this. 45. (2 pts each) What alcohol, and what reagents would you use to make the carbonyl functional group in the following molecules? Give structural formulas.
46. (1 pt each) What are the formulas for the functional groups of a. a carboxylic acid b. an ester c. an amide 47. (1 pt each) Name the following molecules.
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48. (3 pts each) Give the product(s) for the following reactions, and name all reactants and products. + + +
49. (3 pts each) How would you make the following molecules? + 50. List two differences between an aldopentose and a ketohexose.
51. Shown below is a Fisher projection of an aldohexose. Label which carbon corresponds to the anomeric carbon of the cyclic form. 52. Convert the structure above to a Haworth projection, and label your structure as either the α or form. 53. How many chiral carbon centers are there in the monosaccharide shown in question 2? 54. Draw a Haworth projection of glucose. Explain why this cyclic form corresponds to a hemiacetal. 55. Draw a Haworth projection of fructose and explain why this structure corresponds to a hemiketal. 56. People who have diabetes must routinely check their blood sugar levels. The sugar present in our blood is glucose. Describe a test that you have seen in CH 102 that could be used to do this, and explain why it would work.
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57. What is a glycosidic bond? 58. Describe the structures of anylose, amylopectin, glycogen, and cellulose. In your descriptions, include details about the saccharide composition, the bonding between sugar residues, and the polymorphic characteristics of their structures.. Starch Glycogen Cellulose 59. Draw the open-chain structures of D- and L- fructose.
60. Draw the structure of sucrose, and explain why it cannot be a reducing sugar. 61. What are the products from the following reactions? + + Hint: see section 20.3. +

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