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ExamName___________________________________MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.1) Which of the following is produced by the reaction of (CH3CH2)2S with CH3CH2I?A) CH3SCH2CH2CH3B) CH3CH2CH2CH2IC) CH3CH2SCH2CH2ID) (CH3CH2)3S+ I-E) (CH3CH2)3S1)2) What compound is formed when ethylene oxide is reacted with n -pentyllithium followed bytreatment with aqueous acid?A) 2-heptanoneB) 2-heptanolC) pentanalD) 1-heptanolE) heptanal2)3) Which of the following reactions or series of reactions will lead to the formation ofmethoxycyclohexane?A)3)B)C)D)E)1

4) In biological systems, sulfonium salts such as SAM serve what function?A) epoxidizing agentsB) nucleophilic agentsC) crown ether agentsD) esterifying agentsE) alkylating agents4)5) Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?A) sodium (S)-2-butoxide + iodoethaneB) sodium (R)-2-butoxide + iodoethaneC) sodium ethoxide + (R)-2-iodobutaneD) sodium ethoxide + (S)-2-iodobutaneE) Both B and C would work equally well.5)6) What results when but-1-ene is subjected to the following reaction sequence:(1) Cl2, H2O, (2) NaOH, (3) H3O+?A) a meso diolB) butan-2-olC) a 1:1 mixture of enantiomeric epoxidesD) a 1:1 mixture of enantiomeric diolsE) a meso epoxide6)7) When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product isreacted with NaBH4, what is the primary organic compound which results?A) 1-methoxypentaneB) 3-ethoxypentaneC) 1-ethoxypentaneD) 2-ethoxypentaneE) 2-methoxypentane7)8) Which of the following corresponds to the COC bond angle in dimethyl ether?A) 94° B) 60° C) 180° D) 122° E) 110°8)9) What is the major difference in the structure of the product formed in a Grignard reaction when analkyl magnesium halide (Grignard reagent) is reacted with an epoxide rather than an aldehyde orketone followed by work-up with H3O+?A) The alkyl group from the Grignard reagent will be bonded to the α-carbon of the alcoholproduct.B) The alkyl group from the Grignard reagent will form an ether product rather than an alcoholproduct.C) The alkyl group from the Grignard reagent will be bonded to the β-carbon of the alcoholproduct.D) The epoxide will protonate the Grignard reagent resulting an alkane product.E) Two equivalents of the Grignard will result in the bonding of two alkyl groups to theα-carbon of the alcohol product.9)2

10) Which of the following reactions or series of reactions will lead to formation oftrans-2-methoxycyclohexanol?A)10)B)C)D)E)SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.11) Provide a structure for the expected product of the following reaction. 11)12) Provide the structure of 4,4-dimethylpyran. 12)13) Draw structures which show the hydrogen bonding interaction that exists between waterand dimethyl ether.13)3

14) Provide the major organic product of the reaction shown below. 14)15) Provide a common name for the following compound. 15)16) Provide the structure of 3-methoxyfuran. 16)17) Provide the major organic product in the reaction below.17)1. NaCH3CH2CH2OH2. PhCH2Br →18) The Williamson ether synthesis occurs by the __________ mechanistic pathway. 18)19) Use arrows to show correct electron flow in the mechanism for the reaction below.Include all intermediate structures correctly drawn with formal charges.19)20) Anisole is known by two other names. Give either of them. 20)21) Provide the major organic product of the following reactions. 21)4

22) Provide the structure of the fragment in the mass spectrum of dipropyl ether that resultsfrom α cleavage.22)23) Provide the major organic product of the following reactions. 23)24) Show how propyl cyclopentyl ether can be prepared starting with cyclopentene and usingan alkoxymercuration-demercuration route.24)25) Provide the major organic product of the reaction shown below. 25)26) Provide the sequence of reactions by which propoxycyclohexane can be prepared througha Williamson ether synthesis.26)27) Provide the major organic product of the following reactions. 27)28) Show the best method for preparing methoxycyclopentane via the Williamson ethersynthesis.28)29) Some ethers can be prepared by heating the appropriate alcohol in the presence of sulfuricacid. Can di-sec-butyl ether be prepared from sec-butanol by this route? Explain youranswer.29)30) Provide an acceptable name for the compound shown below. 30)5

31) Provide the major organic product of the following reactions. 31)32) Provide the structure of the sulfonium salt that results when (CH3CH2)2S reacts withCH3CH2Cl. Through what mechanistic path is this reaction occurring?32)33) Provide the major organic product of the following reactions. 33)34) Provide the major organic product in the reaction below. 34)35) Provide the major organic product of the reaction shown below. 35)36) Provide the major organic product of the reaction shown below. 36)6

37) What reagents are necessary for the following transformation? 37)38) Provide the necessary reagents to complete the following reaction. 38)39) Provide the major organic product in the reaction below. 39)40) What term is given to the sulfur analogues of ethers? 40)ESSAY. Write your answer in the space provided or on a separate sheet of paper.41) Provide the major organic product in the reaction below.42) Provide the major organic product in the reaction below.CH3CH2CHCH21. Hg(OAc)2, CH3CH2OH→2. NaBH443) When ethers are stored in the presence of oxygen, what explosive materials can result from autoxidation of theether?44) What complex results when BF3 is dissolved in dimethyl ether?7

45) Suggest a reasonable mechanism for the reaction shown below.46) Provide the major organic product in the reaction below.HOCH2(CH2)2CH2BrNaOH47) Provide the major organic product in the reaction below.48) Propose a structure for the ether of formula C4H10O with the following 1H NMR signals: δ 0.95 (triplet, 3H),1.52 (multiplet, 2H), 3.30 (singlet, 3H), 3.40 (triplet, 2H) (ppm).49) What is the stereochemistry of the product of the acid hydrolysis of trans-2,3-epoxybutane?50) Can one prepare di-sec-butyl ether in good yield by heating butan-2-ol in the presence of sulfuric acid?Explain.8

Answer KeyTestname: 12B‐ETHER‐EPOXIDE1) D2) D3) E4) E5) B6) D7) E8) E9) C10) B11)12)13)14)15) allyl ethyl sulfide16)17) CH3CH2CH2OCH2Ph18) SN29

Answer KeyTestname: 12B‐ETHER‐EPOXIDE19)20) methoxybenzene or methyl phenyl ether21)22)23)24)25)26)10

Answer KeyTestname: 12B‐ETHER‐EPOXIDE27)28)29) No. sec-Butanol is a secondary alcohol. Secondary and tertiary alcohols predominatly undero elimination whenheated in acid.30) 1,4-dioxane31)32) (CH3CH2)3S+ Cl-; SN233)34)35)36) Br(CH2)6Br11

Answer KeyTestname: 12B‐ETHER‐EPOXIDE37)38)39)40) sulfides or thioethers41)42) CH3CH2CHCH3∣OCH2CH343) hydroperoxides or dialkylperoxides44) (CH3)2O·BF345)46)47)48) CH3CH2CH2OCH349) meso12

Answer KeyTestname: 12B‐ETHER‐EPOXIDE50) This would not be an appropriate method of preparing di-sec-butyl ether in good yield. When butan-2-ol, a 2°alcohol, is heated in the presence of strong acid, the major product is 2 -butene, the elimination product.13