Exam3Test3 - Chemistry 322a/325a-2 Name J r Exam No 3(1(15...

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Unformatted text preview: Chemistry 322a /325a -2- Name J\ ' r Exam No. 3 (1) (15) Complete the chemical reactions beiow by providing the missing organic produciz within each box. YOu do not need to Show the byproducts of the reactions, or any mechanisms. Be carefui to Show stgreochemical details in the products wherever they are important. H3 1‘11“" 9 “ “' I (A) /3\C m (31“.? LXLBSb 1-12 CHBCHQ Pt, ethanol opkicaily active giizczqucm CH nv 1 WMO (BL " 3}}. K31» acetone argcflz '- single enantiomer (opticaiiy active) ($71-$14) (Q9_.9Rt;i9a_1a9fiyfly) "$13 ~- (c1) Hun-cf ‘_ Why—Mai” 1 / CHZCHZBL‘ acetonitr-ile Céfig single emntiomer piqgcm .. (D) Brigg“ __ _ WWZCWI “K, g (“-3 ethanoi single enantiemer {M a; C6H14O (optically active) fi. if NaOH (3:) . a (CEgbCH H20, acetone (3914180 (3%}?_.E1.i_'ri1§ter€0m¢¥) .1 31.. 3 Chemistry Baa/(32511 »3— Name 3‘3"“ Exam No.3 12) (15) . (A) (10) Circle the structures beiow that are chlrai. CH OCHCH CH CH C H 131-1615511311, I 11111233131311/131230333 1. 3 C33 3 3 3- 333 __ 3 9111.115)? “ -- E-CHECHEQHCHECOOH} CHE CHC 1311:0011 1- E (3333 33333 ECH CH HQH<LH ) CHE)ECHCHECHCHECHCHE 3 2%}E 3 2 I}. 3"3 3 2 (B) (3) The compound. 2~amino~1 ~pheny1propane (1), more commonly caiied amphetamine, is (“11117211 While both enantiomers are stimulants of the central nervous system the (R) stereoisomer is more active Compiete the stereodrawing beiow for (R)- --2 amino—L phenyipropam by phasing the four atoms ,r’ groups around the sterecicefiter 111 the order requ‘st'ed where (A)1s Hie Eughest priority and (D) 15 the lowest priority group HH2 C EHECHEC Ho HE H (R)~2—ami11o-1 w1911erzyipropame (C) (2) If optically pure (R)- --2 -amino 1— —pheny1propane (100% ee) has a speczfic rotation of 15 [OLID‘ $1493 ~E1- .1. what is the mixture of (R) and (S) enantiomers in a sampie of amphetamine that shows 15 1D [01 : +20O answar Chemistry 3223/ 325a ~4— Name ‘ ' Exam No. 3 (3) (20) Circle the answer that correctly completes each question or statement beiow. (A) The general structure of the prescription drug Darvon (an analgesic) is show below. 3? v.Q'—CCH2CH3 qHScezqu(CI~r3)cH2N(cr~tg)2 1" . CSHE H. J Darvon (circle correct answer} ~There is one stereocenter in Darvon and the number of stereoisorners is 2. —There are two stereocenters in Darvon and the number of stereoisomers is 2. «There are two stereocemers in Darvon and the number of stereoisomers is 3. .3 «There are two stereocenters in Darvon and the number of stereoisomers is 4. K I t <"" l (‘6) Which statement is correct about the structures below? -H is the meso-d-iaster-eomer. .3- l {L «H and III are the enarztiomers of the meso diastereomer. ; «0113y- —EV 15 the mese— dies-tereorner 1 £3} «E and III are thes same stereoisorner which rs the meso diastereomer. (C) The compound 2,3,4wtrich.lor0pentanoic acid had three stereocenters as shown in the structure beiow. The configurations at the sfereocenters for four stereoisomers of this compound (there are more) are shown (1, 11,131 and 3V). The two stereoisomer that are enantlornersare coon goon coon coorr “HQ 1‘ t t %HC1 F B 33 tor—1C1 F P 3’ CH3 CH3 CH3 CH3 . . . I 11 III 2,3,4wtrrchloropentanorc ac1d {circie answer) I and H K II and “III-T1 III and IV II and IV Chemistry 322a /325a ~5~ Exam No. 3 (3) (301113331. (D) Three Fischer PIOEECfiOH formulas of 2~butanol are Show r1 138303337. Cfizcr—ia 313%.. 0H1“ ,a CH {circle correct answer) ._ ’1' ‘1. , -The stereocenter 121.1 is (S) and the other formula that is (S)-\.is..II-.--- .. .' E)/I 31113: stereocenter in i is (S) and the other formula that is (S) is III. -The.stereocenter in. I is (.R) and the other-formula that is (R). is H. —Tha—stereoce:1terjo I...ie..(R)3-and the other-formula that 153(3) is III. . (E) The structure beiow that represents the most stable conformation of cis-‘l-isopropy1~4~methyicyclohexane is {eteie answer beiow) {c113}c11 c113 {CH3)CH 33"- (F) The energy barrier of almost 11 keel/moi during interconversion of the chair confon'naiions of. cyciohexane is associated with the highiy strained conformation (Circie answer below) wad) P1333“ pure boat __ twist boat ‘3 half chai1‘ __ - (G) In the reactioo of methyl iodide with sociium methoxicie m methanoi, when the concentration of methyl iodide is doubled and the concemration of sodium methoxide is doubled, the reaction rate wili circie answer below CHBI + NaOCIwi3 W increase by factor of 2. zhcrease by factor of 4'.- 3 \‘h\\ {[1311- 3- slow down by factor of 2. not Change. Chemistry 3223/325a ~5- Name “___L.__' '. Exam. No. 3 ‘ (3) Contd. (H) Which statement correctly describes the reactivities of the foilowing aikyi bromides in an 8N1 reaction? [5r CHgCI’ICHZCHs (CH3)3C«BI CHBCHzCflzCI-IQBI: I II III (circie correct answer} ifhey wili a1} react at the same rate. -The reactivity order will be I>II>III —The reacfivity order will be III>I>HII —The reactivify order WiII be II>I>III (I) A study of a nucleophflic sobs’titotion reaction shows the foilowiag results. R-X + Nu WWW R—Nu + X W initiai IR ~_X]__ \ Initial; [-Nuj Initial Rate (mole 1:1 5-1) 0 050 M . 0.050 M 1.0 x 10“ 0.200 0.050 2.0 x 3.00. 0.200 0.100 2.0 x 104 0.200 _ 0.200 4.0 x 10"1 W {circle correct answer) 7100831011301 for this reaction is 8N1 aod the rate - k[RX] INu‘] “The symboi for this reaction is SNl and the rate 2* HEX] - The 53311th fol thls reaction is SN? and Ihe rate “1([RX] {Nu ]. If} 1e symbol for this reaction is SN2 and the rate. . m..I<[RX]. -- .- (j) The Stabiiity order of the carbocations below is 975-13 + + CH3qCH2CI—12 " CH39HCH2CHCH3 CHSQCHQCHECHB CH3 " CH3 (Circle answer) I>II>IH " III>II>II mom-t III>Z>II Chemistry 322a/325a ~7~ Name Exam No. 3 - (4) (19) When (R)-(+)—glycera}dehyde (I) (the dextrorotary enantiomer only) is reacted first with sodium cyanide in water, and then aqueous acid and heat is a hydrolysis reaction, two producz‘s are formed (A arid 33). Both have the general structure of 2,3,4— trihydroxybutanoic acid (shown below). These two products agemseparabielbxwoidnigagy physical_._xassaess and eachis.satisallyasiivs=. "” 9? QH C: (i) NaCN/HZO {ii} “30+; 1120, heat .. - "MM MM 1' 5‘ OH hydrolysis (LE—1201i (I) (RH+)~giyceraidehyde "f‘wo products are formed tha£ are. separable by ordinary physicai methodsfiach is opticaiiy active. When the separated 2,3,4—trihydroxybutanoic acids are each reacted with nitric acid, ail oxidation reactioa occurs yielding tartaric acid products. A yields an optically inactive tartaric acid whiie B yieids a levomtatory tartaric acid as shown below. (POOH (FOOH smog agaoe seams} WM, ~ 1'1” 0,12. i 5: if?" OH 2 m H'a“ on " w ‘dat'on ” Ci-igGI-i} ml } coon tartaric acids Opiifiéiixifi‘gfle (—)—i‘artaric acid C optacafly inactive tartaric-acid -- tartaric acid I) («)«tartaric acid (A) (4) Compiem the siructures for the tartaric acids in the boxes labeied C and 13 above. (13) (4) Based 011 the structures for C and I), complete the stmctures in the boxes labeieci A and B above. (C) (2) What is the term that describes the stereochemical reiafionship between A and B and C and D? \ _ :=: -r._ 5 i . .. Chemistry 322a /BZSa -8— Name “Aw” . Exam N0. 3 (5) (10) Write out the best possible synthesis of. 2,2-dimethyl»3~heptyne by sele'eting starting materials and reagents from the allowed starting materials in the hex below. Your proposed synthesis should be a series of chemical equations clearly showing startirzg materials and products for each step. It is not necessary to ShOW any mechanistic details. 133%5 allowed materials " H. (FHs Cngem feezmzeeg CH3CH2CH2C:CH CH3 fi—CH C1913 l 3 CflsCH2CHzBr NaOCH2CH3/CHQCH20H 2,2~dimethyl-3~heptyne (91,13 ‘ NaNHz/liq. NH3 sic-a. . CE3¢"BI CH3 g! ' Chemistry 322a/325a "9— Name 5 I " at". :1 J Exam No. 3 5' (6) (3.5) A substitution reaction A + B-C WW AA?» + C is a one-step reaction It 25 exergonic by 10 kcal/mol and has a AG:: 8 O Real/mo}. (A) ('10) Draw the free energy diagram for this reaction below Note the free energy axis is relative energy referenced to the starting state In your diagram. Show the product state, draw a quantitatively correct free energy diagram connecting the reactant and product states identify the transztwn state with am progress of reaction M ( (gee/fa?) (B) (5) Expiain the significance of the "energy factor” in terms of the above free energy diagram. ‘ibfi Y' .9"- “'\ 5- '- -' "ii ‘I- ‘I 5, r -, i g" .n- i' . - . ‘f 1 II 3 ' 1 - ! . .' . ., l ‘K {a {IVY ( {1‘ i. E: \' .:--\.-' l:. is“; ‘i‘ .. .' .1". {IN-J _ i: .5 3 ”.5 5.. _ :. f..:_ .- -=_ . { .4 a t t E _ K x l ( ; t :; EX I: .‘ 1.. \ i . i . 13 . , f i . i; 1‘ a. M U J I” \ K } {cl-3 1-“ k is a i) a Chemistry 3223/3253 -10_ Name W .. Exam No. 3 (7) (15) Compound I reacts rapidly in a hydrolysis reaction (acetone is a co~soivent) to produce a mixture of two alcohol products. The initial} rate of this reaction is given by rate 2—: k[l]. at 3 (A) (4) Provide cieiailed structures for the two alcohol products in the boxes below. CH3 3 19120 m—n-mm—m—mm—‘pv acetone H CH3 two alcohoi products (’8) (2) How are the two products related? Constitutional isomers, ena-ntiomers, or 1 . diastereomers? :s.- - ., -. (C) {1) W12 these two products have identical or different physical properties? “-571? (D) (8} Provide a mechanism for this reaction as a series of chemical} equations. Your mechanism must include and identify the rate~determining step for this reaction, and Show how two alcohol products are formed. Use the curved arrow formahsm. [If I [E { f 3" 5' : --. is: .. “ 1‘ f .. a .- - 3 .5.- t” ' . __,.-r-’-"" {IE-3 I I. 1/" f‘ I 3’ -...L_‘- l r" -- = -. ,/ -t-w I / "\__ (If a x / _ ‘= \-. . , {it /~ . I 1‘? ”ti,” - 'I ' H x" / /, ,f x [I [1. -,\ g, ”r Ir { f . \ := . .c \ \t’ xi“! I [I 3: {:y/‘n..:\ \: f t E i 1 f ., t 3 3 i 3 . E I .. J {t K‘\ - . ./ ...
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