W16, 109B, Bruice, MT2 - /Z I 161911113195 llmms What is...

This preview shows page 1 - 8 out of 8 pages.

You've reached the end of your free preview.

Want to read all 8 pages?

Unformatted text preview: /Z/ I. 161911113195, llmms What is the majm pmducqs) of each of the following reactions? Or if no reaction will occur. 50 state. OH 0 O 1 “ ~ HCI N we * N a. C + C EN ———- l , :- (Jul 3 O (7”3C}12/’3)\H excess ”WM ‘ 0" b \ "L, I O ICI‘ excess . KC? UR H \ 1_ CH MoBr c x + (MLO b. CH 3012/ OCHZCH3 ___3_:> W, CU” 2; U1 5 2_ H3O + UAS 7K) O. CO 1_ CH3CH2CH2MgBr (I) C. ——————> x 2 2.1130+ Ho / CMZ (in (ME) 0 ll (1 HO C CM / ‘ ’ CH3CH2CH2C EN + H20 —_—.' .7 K, i 2 3 q A .1 ' onngw’t 0 (,1 g} f? .9 C C ,_ C , C o e CH3CII>\7/CH3 CF3’ ‘00— CM”); 9* 0 ‘(Ma T 012, o ‘ CH3 w’b f, \@ LEAH!4 O H 2 3 m wamchZOH + (1M?J W7, 30 / \ 3 ‘OH A O I + OH ———> C HLO 2. (3 minutes, 8 points) a. Circle the compound th/aljmqre reactive towards reaction with nucleophiles. 0\k \ l (.3. <3 1. CH3CH2/ \C1 or CH3CH2/C\H O (|:| 01' 2. CH3CH2/ \CH3 b. Draw the structure of malonirc acid C} gefi 3 C, 7, U )\/D\ 3 , r * G H’ O O H a o o o (\ f l \L b. Draw the structure for gacyl phosphate 0 p M. P A P u If! /} \N/. \fi/l O / P \ O" a .. o 0- 0! A ’ O O 0 c. What phosphate grOup is attacked to form an acyl phosphate( (1, fl, or y)? 3. 3 minutes 4 ints Relative priorities: carboxylic acid > amide > ester > aldehyde > ketone > alcohol ‘ .Zvive two names formant/29’ the following compound: (I? .) ‘l—bromo borwnaJl c BrCH CH CH / A 2327’ 2 '\H 1),),‘bf0m0 burgxafl 7 lb 0" b. Give one name for each of the following compounds. 4. (6 minutes, 16 gointgl What is the major product(s) of each of the following re a- + (C6H5)3P.¥_-CHCH2CH —— ' 04012043 * (Co ”545 P30 : 3 actions? Or if no reaction will occur, so state. Z 0 b. CH3CH2CH2 CH3 2—...H3O+ 04?, an an UM OJ :5 Z q n __ Raney Nickel c. L H3L,£{2C=N + H2 ———-— (Luv) (Li/{Z Q41 M V‘ 2, w 0 6 g 2:: Z d- C}13(:}{:CH/ \C1 + CH3OH —_"' (114ng CH/ 004?), O excess 1' ' -\ e. 1. CH3CHZSH/HCI fl : § * 2. H2/Raney Ni O 1 9k 0 ('3' _ f. CH3CH2/ ‘OCH3 + C] " MO RXN Z- 0' 0 ‘ (‘5 c':' _ 9 Z“ o l g. CH3CH2 ‘0’ \CHZCH3 + CH3OH / Q +_ H ‘ warm 0H /C" 0450 CMZL _ 0 h. , Ira + 0410””) + CH3CH2NHCH2CH3 fl— / Z w _(__5- 6 mminms'miasifltsi a. Show the mechanism for the following reaction. (Show all proton—donating species as HB+ and all proton-removing species as 2B) 09 0 ‘”—”"‘“ + ll N H5313 (I). C + H20 ‘r—h‘__ C + R’ ‘NHCI-I3 LCD R’ ‘OH b. Show wt. t 6. 5 minutes 6 are slow steps by drawing a circle around the reaction anows of each slow step. ints Show how each of the following compounds could be prepared from the given starting materials. E ii a. C CHSCH-Z/ C\NH2 CH3CH2/ \Cl 0 . A We» :19 ,c 0MyM7, ‘OH (R b. CH3CH2CH20H —-—-- /C\ 'fOl—l ; . Ci) 5 H ‘H’ L‘ {sigma/i5 g + NV‘CL'UHE ‘ j/ R/ \oH WW @ .. c, -Mtou?) ~> R—~C - NHCM’b fl R‘C‘t—‘szb kadlfg ' ’t O” \* HIE 0” _L_..___7: 6 minutenolwgénlsl What is the major produci(s) of each of the following reactions? Or if no reaction will occur, so state. 0 0 O (“3 H ll || CH3CH2 \ ‘ w? 013 l l/ b \C=NO + H20 EFL. NHz + cu o” ‘3 ' 024 ® CH CH CH ’C\CH + NH H2 UM) d“ wk — (T ’ [b ——. 3 2 2 3 3 Pd/C N Ht 0 0p) /}': 1.NaBH4 '5’ H —-—> / @CH3CH=CH 2.H20 CH5QH= CH \ 0 u + WgoH g + CH CH CH OH £1... C\ 3 2 2 / e. CH3CH2/ \OCH3 excess A 01% (14/; 0 (“1,041 W3 0 éflvjfi) ” 1 LiAlH . C _.._..' 4 H CM OM 1'. CH3CH2/ \NHCHZCH3 2.1120 0M5 0’” (M1 M [L 5 o 0 g‘ l.(CH3CHz)2CULi 0 C141 OLA?) —-—p 2, H30+ o r, 0 IC1 ([1 1 NaBH4 SM (,3 7( '1 013212 3\CH2gH2/[g @ 2 H20. CM?) W104 CHLWl 0": I L} Wm§—- ' 2 . . ' _ Cl l I 144 L O C / ‘ N M cm e K MU} 8. 54 minutes, 4M21§1 a. Label the following compounds in order of decreasing reactivity in the first slow step of a nucleophilic addition—elimination reaction (formation of the tetrahedral intermediate). Label the mot reactive #1. O 0 0 /Ié\ y: ii ” é/ cH3 O© .. CH3/ \0 CH3/ \0©—G iris/V ‘ '5 sect b. Explain why an amide cannot be hydrolyzed under neutral conditions but can be hydrolyzed under acidic conditions. Uhdfir YlCUWLQ COYlCHfiO‘u’lS/ 1km, WHO cop Vie kwswon 0190 base ~‘ro Maud W HM, WUCUO . ?&1%.>a)tt0dcgjl4m (C‘OlCXflJ/ld’wooldduswe Form, i Rod prOrDi’lMS H/Lo mil—r0 ‘ ,mowo i+-a 9.5minutes 12 oints W ‘C Ulna/ W I :1. Which statement best describes the aggregation of long-chain (R groups with 16-20 carbons) carboxylate ions in an aqueous solution? (Join; cow banal OW side, Doll/(fir 044% lowly . no fly form micelles with the polar carboxyl groups on the outside and the polar alkyl groups on the inside of the ' elle. A>Q'1hey form micelles with the polar carboxyl groups on the inside and the nonpolar alkyl groups on the outside of the ‘ icelle. \/X They form micelles with the nonpolar carboxyl groups on the outside and the polar alkyl groups on the inside of the micelle. X They form micelles with the nonpolar carboxyl groups on the inside and the polar alkyl groups on the outside of the micell They form micelles with the polar carboxyl groups on the outside and the nonpolar alkyl groups on the inside of the micelle. b. Which of the following statements best explains why protonation increases the rate of ester hydrolysis? 7\ The carbonyl carbon in the protonated ester is less positive than the carbonyi carbon in the unprotonated ester and / therefore more susceptible to electrophilic attack, and the protonated leaving group is a stronger base. \/ 7< The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible Kt? nucleophilic attack, and the protonated leaving group is a stronger base. flhe carbonyl carbon in the protonated ester is less positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic attack, and the protonated leaving group is a weaker base. The carbonyl carbon in the protonated ester is more positive than the carbonyl carbon in the unprotonated ester and therefore more susceptible to nucleophilic attack, and the protonated leaving group is a weaker base. c. Which of the following pairs of reagents will undergo a nucleophilic addition-elimination reaction? 5 an amide + water 7 an acid anhydride and a chloride ion * a carboxylic acid and a chloride ion ’(. an amide + an ester / [fluoride and a carboxylate ion (1. A carboxylic acid derivative will undergo a nucleophilic addition-elimination reaction provided that’ ‘L the incoming nucleophile is not a stronger base than the substituent attached to the acyl group in the reactant. )éhe substituent attached to the acyl group in the reactant is a very strong base. ./ the incoming nucleophile is not a weaker base than the substituent attached to the acyl group in the reactant. )Lthe incoming nucleophile and the substituent attached to the acyl group in the reactant have similar basicities. yithe incoming nucleophile is not a much larger base than the substituent attached to the acyl group in the reactant. e. Which of the following represents the correct order of relative reactivity in a nucleophilic addition-elimination reaction? X esters > acid anhydrides > acyl halides > amides / fiacid anhydrides > acyl halides > esters > amides 7k acyl halides > esters > acid anhydrides > amides )(amides > carboxylic acids > acid anhydrides > acyl halides f. In a transesterification reaction: / an ester reacts with an ester. an alcohol reacts with an est- . an acid anhydride reacts with an alcohol. an ester reacts with an amine. an ester reacts with water. 10. (fi‘lili‘gyj‘gs, 16 points] What is the major product(s) of each of the following reactions? Or if no reaction will occur, so state. (I). o CH CH /C\ + H 0 HC] It a. _. _ 0 0H 0 ll “ C ______._ C 4» CA, . CH CH / \ + 0/ / \ b 3 2 Cl curb GU”; O y (5) 0 II HCI c. HOCHZCHZCH CH2COH ———— i 7, 3 S (3 O [L c'! H 0 319.. c H / \ + 2 . 0 d. CH3CH2 OCH3 excess CVi?) W”) o 1, HO_ C00 H e- NH 2. CH3CH2CH Br l 7" 015 (M1 (M1, NH; _____—1. / , 3. H20,HC1, A COOH o O _ ‘3 A “ + 0460’ C _. f. CH3CH2/ \OCH3 + CH3CH2NH2 0H5 (M4 ‘ NH 042 CW5 O 0 II C ' _. CH CH g- CH3CH=CH/ \CH3 + ”3' 93. (5r 0 ” HCI C + CH3CH20H —> _ 11- CH3CH2/ \CH3 excess CW5 (LU): ‘ CW3 ...
View Full Document

{[ snackBarMessage ]}

Get FREE access by uploading your study materials

Upload your study materials now and get free access to over 25 million documents.

Upload now for FREE access Or pay now for instant access
Christopher Reinemann
"Before using Course Hero my grade was at 78%. By the end of the semester my grade was at 90%. I could not have done it without all the class material I found."
— Christopher R., University of Rhode Island '15, Course Hero Intern

Ask a question for free

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern