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2002 Final - Winter 2002 Chem 266 Chem 266 Final...

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Unformatted text preview: Winter 2002 Chem 266 Chem 266 Final Examination December 6, 2002 On the computer card, circle the best choice A to D for each of the 50 questions which follow. There is I mark for a correct answer and 0 marks for an incorrect or missing answer. Under ID number, put you ID number. Under section put 001 (for Dr. Maekay’s section) or 002 (for Mr. Forsey‘s section) Do not leave blank. Under Card Number, leave blank. Remember to put your name and course number on the right. Calculators and/or molecular model kits may be used by individual students but may not be shared around during the examination period. Note: Make certain that all ofyour answers are properly indicated on the computer card. Only the answers marked on the computer card will be considered in arriving at your final exam mark. Do not submit the question papers. PERIODlC TABLE of the ELEMENTS (13) (14] "IA IVA AIOmIC Number 5 6 B C 10 81 12 01 Boron Cirhun 13 Al (3) (4) (6) (7) (8) (9) (10) (11) (12) 2693 ms IVB VIB vua vma vma lB na Nun-mum 2‘9 30 Zn 63 55 65.37 Copper Zinc (15) VA 7 N 14.01 Ni1ruoorl So Selenium Winter 2002 Chcln 266 2 1. In the following all bonds and non-bonding electron pairs are shown, but not charges on individual atoms. The neutral molecule is: H .0 I. 0 | . OI '5 I. :o-o: :N—N:o_: H"? - :N=N=N: o0 0' H A) B) C) D) 2. The following are shown with their appropriate charges, but without bonds or non-bonding electrons being shown. The isoelectronic pair (same total number of electrons) from (1) to (4) are: (1) NO+ (2) N! I; (3) r (4)8143 A) (l) and (3) B) (2) and (4) C) ( l) and (4) D) (2) and (3) 3. Diazomethane CH2N2 is a highly reactive and toxic molecule. One ol‘the four electronic arrangements below is NOT likely to be a resonance form ol‘this molecule. H .. .i‘ H + on— H\ o. I. H\+ n x A) :CzNzN B) ,C=N=N: C) ,C=N_N: D) ,C-N=N: H H H H 4. Of the molecules below those which possess a dipole moment are: (1) BF; (2) PF; (3) CS) (4) CF11 A) (2) and (4) only B) (I), (2) and (4) only C) (2) only D) none ofthem 5. The longest C to 0 bond is found in: A) CH30CH3 B) CO) D) CO E) l-I:C=O Winter 2002 Chem 266 3 6. Two and only two, ofthe four compounds, (l)—(4) below, have the same number oftcrtiary (3 ) carbons atoms. These two are? H30 CH3 (CH3)3CCH2CH3 (CP13)2CHCH(CH3)2 H30>O<H (3) (4) (1) (2) A) (I) and (2) B) (2) and (3) C) (2) and (4) D) (3) and (4) 7. In ketene, shown below, the hybridization left to right at C, C and O is best described as: 7 A) SP2, 5132, s B) sp, Sp, spfip H2C=C=O C) 5132, Sp, Sp2 D) sp. Sp. sp 8. [n butudiene, shown below, the maximum and minimum number ofatoms (C and H) which can occupy a single plane in any arrangement ofthe molecule are? (models would be very helpful here) A) 10 and 5 B) lOand l0 H20:CH_CH=CH2 C) 6 and 6 D) 10 and 6 9. The number of different stereoisomers (Le. enantiomers and diastercomers) for the compounds of formula is: A)2 CH3CHCICH=CH-CH=CH2 B)3 (3)4 D) 8 Winter 2002 Chem 266 4 if). The pair of species which are isomers: H3C A) CH3CH=CHCH2CH3 and H i + B) CH3CH=CH"CH2 and CH3CHCH=CH2 H H Br C) >=< and H i CI Cl l CIZHZCI D) CICHZCH(CH3)2 and CH3CHCH3 l l. The pair ofcompounds which are structural isomers is: CH3 Ph Ph CI Ph CI H D H C H A) C) H— 3 H— Ph CI H CH3 CI CH3 D CI H CI B) \Q g D) (6 g 12. The pair ofcompounds which represent a pair ofdiastereomers is: Winter 2002 Chem 266 13. One enantiomer of2-butanol is shown opposite in a Fischer H | CH projection. The stcrcochcmical representation below 3 which has the same configuration is: CHZCH3 OH CH HC H CH HO—cl—CCH3 ‘9‘ 2 3 H30:l:H H 3 H2 H3 H30 OH H30 A) B) C) D) 14. In the compound 2R: 3S-dichlor0butane a C] hydrogen atom is exchanged with a C3 chlorine atom. The resulting compound is best described as: A) mcso B) chiral C) achiral D) racemic 15. The pair ofFischer projections below represents: CH3 H H NH2 HZN CH 3 H CH3 H3C NH 2 NH2 H A) a pair ofmeso compmmds B) diastereomcrs C) enantiomers D) the same compound 16. Consider the structure CH3CHCHCH2CH3 I I Y Z and these specific groups for Y and Z: (I)Y=Cl13,Z=CH2CHJ (3)Y=Z=Br (2) Y = CH2CH3, z = CH3 (4) Y = c1, 2 = Br Which ofthese specific combinations would allow a meso form to be possible? A) only (3) B) only (2) C) only (I) and (3) D) all except (4) Winter 2002 Chem 266 6 l7. l8. I9. 20. 21. The compound which has an enantiomer is: Cl CH3 A) CH2FI C) H3C ¢\\\\H The only true or only untrue statement in the following is: A) A molecule with an internal plane of symmetry cannot have a different mirror image 8) A chiral molecule must have at least one chiral carbon atom. C) An achiral molecule does not have a mirror image. D) In a pair ofdiastcreomers one must be chiral. The alkaloid strychnine shown below is a central nervous system stimulant in low doses and a potent poison in higher doses. The number ofchiral carbon atoms in strychninc is: A) B) C) B) 0390\le The configuration of the carbon at thejunction point of the 5, 6, 6 rings (arrowed) and ofthe carbon to carbon double in strychnine (Q 19) are: A) R, E B) 5,5 C) 12,2 D) 5.2 In the symmetrical (not twist) boat form of cyclohexane the total number ofH/H eclipsing interactions on adjacent carbon atoms is: A)2 B)4 C)6 D)8 Winter 2002 Chem 266 23. 24. 25. Chair-chair interconversions of equal energy are only possible in the case of: A) l-ethyl-l -methytcyclohexane B) all cis-l ,2,3«trimethylcyclohexane C) ethylcyelohexane D) cis— l ,4-diethylcylcohexane The major alkene obtained when 4-bromo-3,4-dimethyIheptane is heated with potassium cthoxide is: A) /\(i\/\ c) /\i/U\/\ (E + Z) B) W D) W (E + 2) (E. + Z) The fastest reaction in an $32 substitution of Br when I-brombutane is treated with the nucleophile Nu in the reaction: /\/'\Br + Nu_ —> /\/\Nu + Br— A) CF13803 B) CH2=CH C) Cl D) CN The fastest 8N1 reaction in a substitution reaction with water as a nucleophiie in R-CI + H20 —> ROH + Cl + HT is when R is: CH3 I B) (CH3)3CHCH2C1 D) <:>—CHZCH2CI Winter 2002 (Them 266 8 26. 27. 28. 29. The three isomers ofC6H13Cl. shown below are reacted with NziOCH3 in CH3OH in a nucleophilic substitution reaction to give ether C6H130CHi (l) l-chloro-4-methylpentane (2) 2-chloro-3—methylpentane (3) 2-chloro-4-methylpentane To the extent that these reactions go by an 8N2 mechanism the relative rates ofthc reactions (fastest to slowest) is: A) (1)>(2)>(3) B) (1)>(3)>(2) C) (2)>(3)>(1) D) (3)=(2)>(l) lt‘the nucleophile CH30 in Question 26 is replaced by the very bulky base, (CH3)3CO , elimination dominates substitution and an E2 reaction takes place. if the three chlorides in question 26 are heated with potassium I-butoxide in [- butanol by a strictly E2 process the chloride which will produce one alkcne and one only is: A) (l) B) (2) C) (3) D) none of them The doubly unsaturated dichloro compound below is warmed with one equivalent of sodium methOXide (NaOCHg) in methanol. The ether product that forms is: A) /O\M/\o/ C) Cl \ / W0 0 \ A high yield reaction for the synthesis of l-butyl bromide is: A) heating l—butanol with sodium bromide and sulfuric acid B) treatment of l -butenc with HBr in the dark C) treatment ofn-butene with Bl'g D) treatment of l-butylmagnesium chloride with sodium bromide Winter 2002 Chem 266 9 30. 31. 32. 33. Order the bases (l)-(4) in decreasing base strength, i.e. from strongest to weakest: (l) CH38 (2) CH30H (3) CH30 (4) CHgNH A) (3)>(l)>(4)>(2) B) (2)>(1)>(3)>(4) C) (4)>(3)>(|)>(2) D) (1)>(3)>(4)>(2) The alcohol most likely to give an alkene of rearranged carbon skeleton when heated with acid is: A) >_<m C) >[—/ OH B) %—€H D) OH The. most stable carbocation is: 9Hs+ A) H3C—(I3-CH2 (3) CH3 + + + B) CH2=CHCH2CHCH3 D) Q—CHCH3 The sulfonate ester below is heated with NaOCltCH; in ethanol in an E2 reaction to give alkenes as products. These are most likely to be: 0 H H A) H/Q only C) mostlyAbutsomeB H30 H B) HQ only 0) HacceH4ost’Q only i CH3 H30 Winter 2002 Chem 266 10 34. 35. 36. 37. A radical reaction which is not at all likely in thc halogenation reactions of methane (CI-L; + X3 —> CH3X + HX) is: A) ‘ CH3 + Br; —> CHgBr + Br. B) Cl ‘ + CH4 —’ CH] ' + HCI C) I 0 + CH4 —> CH3 - + H1 w’“ D) CH3° + F2 —* CH3F + F. A mixture of i mole of propane, one mole of2-methylpropane (isobutane) and one mole of bromine is irradiated with UV light until the bromine is used up. One monobromo compound dominates the reaction products. That monobromo compound is: A) 2—bromopropane i B) 2-bromo-2-methylpropane C) l-bromopropane D) l-bromo-2-methylpropane I,l-Dimethyleyclohexanc is treated with a limited amount of chlorine under the influence of UV light to give all possible monochloro compounds. The number and kind ofmonochloro products (chair/boat and axial/equatorial consideration not necessary) expected is: A) six of which two are achiral and four are racemic B) five ofwhich one is achiral and four are racemic C) four of which two are achiml and two are l‘accmic D) four all of which are racemic Cyclopentylmethy[magnesium bromine, shown opposite, 0-— .g’“-- is treated in ether with cyciopentangil The major organic CHzMQBr .. product after a dilute acid work up is: / __.._...—+- on M O‘ O Gem-GO B) O’CHz‘O D) O‘CH27O Ctr“ t HO 2‘1 Winter 2002 Client 266 l l 38i 39. 40. 41. The tertiary alcohol, 1,1vdiphenyl-l-butanol, shown below‘ is made by one ofthe {our Grignard reactions given below, an aqueous acid work up being involved in each case. That reaction is: Ell) CH3CH2CH2- g_OH Ph A) 2PhMgCl + Cl‘lJCl'bCHzCHO X B) 2Pl‘tMgCl + CH3CH2CH3C02CH2CH3 --h.- C) CH3CH2CH2MgCl + 2PhCI'IO 3», D) CH3Cl12CIigMgCl 'l PhQCHOH y: (>E,¢Mli .---l L'fi J The alkene which on hydrogenation over 3 Pt catalyst will give a racemic hydrocarbon is: ‘54 A) 3,3-dimethyleycl0pentene 0+ he“; B) 4,4-dimetltylcyclopentene '2: f l C) 2-methyl-l-butene Jr i‘x/‘r, - - ‘ "HTS: , D) 2-ethyl—3-methyl l butene/ 2W, 6‘“ The die-rte opposite is reacted with excess of hydrogen iodide. The most likely products are (structurglLsgmgns only. beingmnsidered, not Stereoisonigs) ' I a”, __ .t ' I . B) O D) Ia mixture ofB and C I An alkene is Subjected to reductive ozonoiysis (03 followed by zinc powder in dilute acetic acid) and gives the keto aldehyde below as the only organic product. The structure of‘the alkene must have been: “”1 W“ <3“ 0 o A) CH3CH2CII=CHCH2CH2CHO C) m“ F0 0 ll 8) H3CHZC~C-CH20H2CH=CH2 D) —@ Winter 2002 Chem 266 42. l-hutene is treated with a solution of bromine in wateri The major product expected is racemic: A) i-bromo-2-hutanol ’ ' Qt ‘ B) 2-br0mo- l -butanol Ii 1?, ~:_ C) i,2-dibrom0butane r‘ ' D) 3-bromo- l -hutene 43. The order ofdeereasing acidy, most acidic first, of the four benzene derivatives (1) to (3) is: . O M“ OH OH OH 1"!) I‘f (l) (2) (3) A) (l) > (2) > (3) ”1. 7 :17 i B) (3) > (2) > (Ur/“"- C) (3)>(1)>(2) D) (2)>(3)>(1) 44. Starting with 4-methyl- l -pentene a sequence 01' three reactions is carried out. I) the alkene is reacted with HRr in the presence ofperoxides (01' UV light) 2) the product from (I) is warmed with sodium cyanide, NaCN, in alcohol. 3) the product from (2) is heated with concentrated aq HCI (or H2504). The final product is: CO2H CN A) Ma Q MBr (a; B COZH ' ) M f, I. I" M _ _. { D) __..- 002H If” A/K - /m"£ it! ’2 «.9 Mcfitn H} Ci!“— \ ,r‘hu. '3- » ~ r; “h fir \1. “‘1 Winter 2002 Chem 266 45. ' 46. 47. A) A) B) Equal molar amounts of benzoic acid and potassium hydroxide are dissolved in water. The most abundant of the four species below is. O L0H D) QJLO .- Théf—lac ‘tifiioyopposite is heated with metlixlamine CHgNHz. The major product is: C) 3‘N OH 1430+ B) "OH Which ofthe following reactions does not occur as shown? I {Babe ?C>—> O” <er cold Il/OH Br .3. Q CH2C|2 II/Br (III C) CH3CH2CECH 2H“ CH3CHzg—CH3 "1"“! CI 0 0 H2504 ; /\ D) AAOA ——> OH HO H20 l3 Winter 2002 Chem 266 48. What is the product Z in the following reaction? OH K2Cl'207 M H2364 Z O A) M C) A} OH O B) MK D) no reaction 49‘ What is the product X in the following reactions? 0 O O O A) /\/ll>gl\/\ C) AMA Cl CI MOELA D) /\)Ol\ojl)\/\ 3) 50. What is the product Y in the following reaction? 0 Hgo+ M + HzN-OH +> Y H catalytic ...
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