Test 2 ReviewMcMurry, Chapters 5, 6, and 7Part I. Multiple choice.1. What is the degree of unsaturation in C12H16N2O2?a) 3b) 4c) 5d) 6e) 72. What is the correct IUPAC name of the followingcompound?CH2CCH2CH2CH2CH3CH3a) 3-methylene hexaneb) 2-ethyl-2-propylethenec) 2-ethyl-1-pentened) 2-ethyl-2-propylethylenee) 3-ethenehexane3. What is the correct IUPAC name of the compoundbelow?Cla) trans-2-chloro-2-buteneb) (Z)-2-chloro-2-butenec) (E)-2-chloro-2-butened) (Z)-1-chloro-2-methyl-2-butenee) (E)-1-chloro-2-methyl-2-butene4. What is the correct IUPAC name of the compoundbelow?C CCCH3CCH3CH2CH2H3CH3CCH3CH3a) (Z)-3-(1,1-dimethylethyl)-2,4-dimethyl-1,3-hexadieneb) (E)-3-(1,1-dimethylethyl)-2,4-dimethyl-1,3-hexadienec) (E)-2,3,3,3,4-pentamethyl-1,3-hexadiened) (Z)-2,4-dimethyl-3-(1,1-dimethylethyl)-1,3-hexadienee) (E)-2,4-dimethyl-3-(1,1-dimethylethyl)-1,3-hexadiene5. Which alkyl group below is commonly called an allylgroup?a) H2C=CH–CH2–b) H2C=c) H2C=CH–d) CH3–CH=CH–CH2–e) H2C=CH–CH2–CH2–6. Rank the following sets of substituents in order of priorityaccording to the Cahn-Ingold-Prelog sequence rules.Place the highest priority substituent first and place thelowest priority substituent last.–CH(CH3)2 –CH2CH2CH2CH3 –CH2CHO –CH2CH2OH I II III IVa) IV > III > I > IIb) III > IV > II > Ic) I > II > IV > IIId) I > III > IV > IIe) IV > III > II > I7. Compound A has the formula C10H14. On catalytichydrogenation over palladium, it reacts with 2 molarequivalents of H2. How many rings does compound Ahave?a) 0b) 1c) 2d) 3e) not enough information to determine8. Which of the following alcohols could be selectivelyprepared by hydroboration/oxidation of an alkene?CH3OHCH3OHCH3CHCH3COHCH3CH3CH3CHCH3CHOHCH3 I II III IVa) II onlyb) III and IVc) II and IVd) II, III, and IVe) I and II9. Starting with 1-bromo-2-methylbutane, which of thereaction sequences below would yield 2-chloro-2-methylbutane?a) BH3 in THF; then H2O2, OH–; then Cl2 in CH2Cl2b) Cl2 in CH2Cl2c) CHCl3 in KOH; then KMnO4d) Hg(OAc)2 in H2O/THF; then NaBH4; then HCl in ethere) KOH in ethanol; then HCl in ether10. Rank the carbocations below in order of decreasingstability. (That is, list the most stable carbocation first,and the least stable carbocation last.)CH3CHCH2CH3+ (CH3)3C+ CH3CH2CH2CH2+ I II IIIa) II > I > IIIb) II > III > Ic) III > I > IId) III > II > Ie) I > III > II11. Which compound below is expected to have the largest(i.e., most negative) heat of hydrogenation?a) 4-methyl-1-penteneb) 2-methyl-1-pentenec) 2-methyl-2-pentened) (E)-4-methyl-2-pentenee) (Z)-4-methyl-2-penteneAnswers to Multiple Choice Questions1. D 6. D 11. A2. C 7. C3. B 8. B4. A 9. E5. A 10. APart II. Reactions. Complete the reactions below by drawing any missing reactants, products, and/or reagents. Clearlyindicate the regiochemistry and stereochemistry when appropriate.1.CH31. BH3, THF2. H2O2, OH–2.CH3D2Pd/C3.CH2BrKOHCH3CH2OHAKMnO4H3O+B + C4.CH31. O32. Zn/H3O+5.CH3CH2CH=CH2CH2I2Zn(Cu), ether6. What starting alkene would you use (A) and what reagents would be used (B) to synthesize the alcohol below, usingoxymercuration?OH7.CH2CH3Br2H2O8.CHCl3KOH9.OHOHOOPart III. Mechanisms.1. Draw the structure of the transition state that is formed when 1-methylcyclopentene reacts with BH3 in THF solution. (Only drawthe transition state; do not draw the complete mechanism.)2. Draw the structure of intermediate that is formed when cyclopentene reacts with OsO4 in pyridine. (Draw only the intermediate;do not draw the complete mechanism.)3. Draw the complete mechanism for the reaction of cyclopentene with Br2 in CH2Cl2. Use the curved arrow formalism to indicateevery bond broken and every bond formed.4. When 3,3-dimethylcyclohexene reacts with HCl in ether, one product is 1-chloro-1,2-dimethylcyclohexane. Show the completemechanism for the formation of this product using the curved arrow formalism.5. Write the complete mechanism for the monobromination of