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CHEMISTRY 1152 EXAM IIA Fall, 2011 Kirberger NAME_________________ All notes, books, etc., must be placed out of sight. Please read each of the problems carefully. If something is not clear, please ask. The exam consists of 31 problems worth 3 points each and 1 problem worth 9 points for a total of 102 points. Make sure your exam is complete. Answers should be placed in the space provided. Write legibly--if I cannot read it--it is wrong. Please include an explanation whenever asked to or whenever necessary to make your answer clear. Please put your name on every page of the exam. As usual, no cheating is allowed. Good Luck!!! Chemistry 1152 Exam IIA Name ________________________________ 1. (3 points) Which of the following compounds is correctly classified as a tertiary alcohol? a. 2-methyl-2-butanol b. 2-methyl-1-butanol c. 3-methyl-2-butanol d. 3-methyl-1-butanol ANS: A PTS: 3 2. (3 points) Which compound would be the most soluble in water? a. CH3OCH2CH2CH3 b. CH3CH2CH2CH2CH3 c. CH3CH2CH2CH2OH d. CH3CH2OCH2CH3 ANS: C PTS: 3 3. (3 points) Which of the following compounds would you expect to be foul smelling? a. CH3CH2CH2OH b. CH3CH2CH2SH c. CH3CH2CH2CH3 d. ANS: B PTS: 3 4. (3 points) The boiling points of aldehydes and ketones differ from those of alcohols and alkenes due to: a. Hydrogen bonding between like molecules (aldehyde with aldehyde) b. Hydrogen bonding with water c. Polar bonding between like molecules (aldehyde with aldehyde) d. Both b and c e. Both a and c ANS: D PTS: 3 5. (3 points) Place the following structures in order from lowest to highest boiling point (Ex. X < Y < Z). a. b. O HO H3C CH3 CH3 H3C CH3 c. d < c< b <a___________ d. H3C O CH3 CH3 H3C Chemistry 1152 Exam IIA Name ________________________________ 6. (4 x 3 points) Draw each of the following structures: A. 3-chloro-1-ethoxybutane B. p-phenylbenzaldehyde O H Cl H3C C. O CH3 3-methyl-2,4-pentanediol D. 3-(fluoromethyl)-2-pentanol OH CH3 H3C H3C CH3 OH F OH 7. (6 x 3 points) CH3 Name each of the following using correct systematic names. A. 3-phenylcyclopentanol B. 1,2,3-propanetriol OH OH HO C. diethylether or ethyl ethyl ether OH D. 1,4-dichloro-2-hexanone O H3C H3C O Cl CH3 Cl E. 2-bromobutanal F. 3-ethyl-2-pentanone O H H3C CH3 O CH3 CH3 Br Chemistry 1152 Exam IIA Name ________________________________ 8. (7 x 3 points) Complete the following reactions. If no reaction occurs, write “No Reaction”. a) H3C + OH HO CH3 H2SO4 CH3 H3C o 140 C CH3 CH3 O CH3 HO + H CH3 b) CH3 CH3 H3C H2SO4 H3C CH3 CH3 H3C CH3 180 oC OH H3C HO + CH3 H c) CH3 HO CH3 H3C + (O) No Rxn CH3 d) H O HO O + (O) H3C CH3 H3C CH3 e) CH3 CH3 CH3 H3C + (O) CH3 H3C + HO H O OH f) H H3C O O + H H+ H HO O CH3 H3C H3C g) O CH3 H OH O OH H + 2 H3CCH2-OH Chemistry 1152 Exam IIA Name ________________________________ 9. (4 x 3 points)Identify each of the following as either (a) acetal (b) hemiacetal (c) ketal (d) hemiketal or (e) none H3C H3C H3C H3C O O O OH OH O CH3 _e__ H3C OH H3C O _c__ CH3 H H3C CH3 O O CH3 CH3 _a__ CH3 __d__ OH O H 3C H 10. (3 points) This compound a. Benedict’s reagent b. Tollens’ reagent c. Neither d. Both ANS: D PTS: would be expected to react with: 3 11. (3 points) To what characteristic(s) do aldehydes and ketones owe their ability to form hydrogen bonds? a. having a doubly bonded oxygen b. possessing an oxygen instead of an interior carbon c. hydrogen on the adjacent carbon d. all of the responses are correct ANS: A PTS: 3 12. (3 points) The boiling points of aldehydes and ketones differ from those of alcohols and alkenes due to: a. Hydrogen bonding between like molecules (aldehyde with aldehyde) b. Hydrogen bonding with water c. Dipolar bonding between like molecules (aldehyde with aldehyde) d. Both b and c e. Both a and c ANS: D PTS: 3 13. (3 points) Assuming that molecular weights are comparable, which of the following compounds would you expect to have the highest boiling point? a. aldehyde b. alkene c. alcohol d. ketone ANS: C PTS: 1 Chemistry 1152 Exam IIA Name ________________________________ 14. (9 points) Two products in addition to water are formed in the following reaction. Draw (3 points) and name the products (3 points), and explain why one is the major product (3 points). CH3 H3C CH3 H3C CH3 ___2-methyl-2-pentene__________________ H2SO4 CH3 OH 180 oC CH3 H3C CH3 ____4-methyl-2-pentene____________________ Explain:__2-methyl-2-pentene is major because more carbons attached to C=C bond carbons___ ______________________________________________________________________________ ____________________________________________________________________________ 15. (3 points) Which reaction requires platinum as a catalyst? a. oxidation of an aldehyde or ketone b. reduction of an aldehyde or ketone c. reaction of an aldehyde or ketone with an alcohol d. All of the responses are reactions that are catalyzed by platinum. ANS: B PTS: 3