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CHEMISTRY 150 March 20th, 2013 NAME:_______________________________ B. MacLean __________________________________________________________________________________________ INSTRUCTIONS: For questions that involve drawing organic structures, you may use either line-angle structures or condensed structural formulas. Do not present carbon-skeleton structures for your answers. __________________________________________________________________________________________ Question Mark Obtained Out of A1-10 ________ 30 B1 ________ 18 B2 ________ 22 B3 ________ 12 B4 ________ 12 ----TOTAL: 94 Section A: Multiple choice [2] per correct answer; total = 30 points A1) What factor determines the order of water-solubility for a series of substances? a) intermolecular forces b) intramolecular forces c) boiling points d) molecular shape A2) Which of the following molecules will not undergo oxidation? a) 2-propanol b) 2-methylpropanal c) 2-methyl-2-butanol (3o alcohol) d) sec-butanol A3) Which of the following reactions would be a condensation reaction? a) saponification b) esterification c. acid + alcohol ester + water c) elimination d) hydrolysis A4) Which of the following compounds would be expected to have the highest degree of solubility in water? a) 1-butanol b) 1-propanol c) 1,3-propane diol 2 OH groups d) propanal A5) Which of the following compounds can undergo a hydration reaction? a) 2-propanol b) butanoic acid c) methyl ethanoate d) 2-butene hydration: addition reaction, involves a reactant with a multiple bond A6) Which of the following is a real/correct IUPAC name? a) 2-methylethanoic acid aka propanoic acid b) 3-butanone aka 2-butanone (or just butanone) c) 2,2-dimethylethanol (aka 2-methyl-1-propanol) d) 2-methylpropanal A7) In benzene, there are ____ -bonds. a) 2 b) 3 c) 6 d) none A8) The two compounds, 3-methyl-2-pentanol and 2-ethyl-1-butanol are a) skeletal isomers b) functional group isomers c) positional isomers (see right) d) not isomers A9) Because of their pleasant aromas, ___________ are often included as components of perfumes. a) alcohols b) esters c) ethers d) carboxylic acids A10) Which of the following molecules is a lactone? b a b c d 11) Zaitsev’s rule enables one to predict the major product of a(n) __________ reaction. a) condensation b) saponification c) oxidation d) elimination 12) Which of the following will not have a positional isomer? a) 2-butanone C=O bond can be in only one location of 4-C chain and still be a ketone b) 2-pentanone c) 1-propanol d) 2-methyl-2-propanol 13) Carboxylic acids and ____________ which have the same number of carbons will be functional group isomers. a) ketones b) alcohols c) ethers d) esters 14) When Benedict’s reagent is added to a test tube containing an unknown chemical, the test tube takes on a silvery mirror-like appearance. The unknown chemical in the test tube must have been a) a primary alcohol b) a secondary alcohol c) an aldehyde d) a ketone 15) Which of the following molecules will cause the pH of a solution to rise when added? a) ethanol b) ethanoic acid c) sodium ethanoate d) ethanal the only basic substance listed (c. base of carboxylic acid) Section B: Long-answer problems. Answer the following questions in the space provided. B1. Provide names for each of the following structures in the spaces provided: [18 points] 4-bromo-2-pentanone 1,1,1-trichloro-2-propanol IUPAC: 2-methoxypropane common: methyl-2-propyl ether 2-propyl butanoate (also isopropyl, sec-propyl) benzoic acid 3-methylbutanal B2. Complete the following chemical reactions using appropriate chemical structures. Where more than one product structure is possible, show all structures and indicate which should be the major product: [22 points] a H+(cat) H2O [O] b major H2SO4/180oC c H+(cat) d e f [O] H2O NaOH [R] g Na+ - B3. Complete the following diagram by drawing chemical structures for each of the isomers requested in the fields indicated [12 points] this is the only option here positional isomer any aldehyde of the formula C 6H12O functional group isomer skeletal isomer ketone with a different C skeleton B4. Arrange the following chemical compounds in order of increasing boiling points (i.e. lowest-tohighest). Important: pay attention to the ordering. [12] methyl propanoate, pentanoic acid, 1-pentanol, hexane, butanoic acid, dimethyl ether dimethyl ether < hexane < methyl propanoate < 1-pentanol < butanoic acid < pentanoic acid LOWEST b.p. HIGHEST b.p. Ethers and alkanes of similar molar mass have similar boiling points; hexane heavier than dimethyl ether Esters have dipole-dipole, but no H-bonding Alcohols are H-bonders Carboxylic acids are stronger H-bonders than alcohols