MT1 key (final version)

MT1 key (final version) - K27 Part 1: Short answer /...

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Unformatted text preview: K27 Part 1: Short answer / Multiple Choice (3.5 points) each. 1. What is the IUPAC name of the following compound? 0 GO 55, LL q ~ inmate, ) Pow‘ic‘Muflx 2. Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound? OH WI: (CH3)2CHBI‘ (CH3)2CHCHQBF 0 W0 /U\ 1 2 a. only 1 @ only 3 c. only 1 and 3 d. only 2 and 4 Points awarded Organic Chemistry II - X36.B A X Berkeley Extension EDP#416750 N me February 23, 20 1 1 3. What is the correct assignment of the names of the following functional groups? @4st i m @4331 1 2 3 4 a. acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal hydrate; 2 = hemlacetal; 3 = acetal; 4 = enol enol; 2 = hydrate; 3 = hemlacetal; 4 = enol c d. "u _\-§ 4. What is the major organic product obtained from the following reaction? 1 2 O A st04 O OH o OH HO i : 4 mm (01m 5. What is the relationship between the following two structures? 9.. :0: I 2 M49 M a. tautomers constitutional isomers, but not tautomers sonance structures . stereoisomers Page 3 of 15 Points awarded 6. Which compound is the most acidic/has the lowest pKa? O O O O b 6/0 o 1 2 4 O 7. What is the lUPAC name of the following compound? 0 / OH CZ) " g4wa7l'3’meoFL M90“ 8. Which of the following has the highest boiling point? a.hexane b. 1-pentanol . pentanal tanoic acid 9. Which of the following is the most soluble in water? @cefic acid . pentanol c. butanoic acid d. pentanal Points awarded Organic Chemistry II — X36.B Berkeley Extension EDP#416750 Name February 23, 2011 10. What is the approximate pKa value of butanoic acid? . -2 5 . 15 d. 35 11. What is the major organic product obtained from the following reaction? 0 o 1. LiAlH4 M 2. H30+ W OH OH 0H 0 OH 0 o H 12. What is the major organic product obtained from the following reaction? 0 O OCHZCH ‘ O 14st4 2 —————————————— .m.’ OH H o OCHch3 1 fix \(LOCWCHa 3 4 Page 5 of 15 Points awarded 13. What is the major organic product obtained from the following reaction? 0 Cl W4” OH O \I/‘koci 3 14. What is the major organic product obtained from the following reaction? 0 O O Points awarded. Organic Chemistry II — X36.B % Berkeley Extension EDP#416750 me February 23, 2011 15. What is the major organic product obtained from the following reaction? 0 A /U\N H A )k 2 O N/ W ” AA JLNJL a 7k 16. What is the major organic product obtained from the following reaction? \ lS O 0 Z H O OH NH2 ‘\ Q 0/» 2:63;; 1 2 W l ’W‘ t Y J at \ NH w v2 62:0ij 3 4 17. What is the major organic product obtained from the following reaction? 1) 2 eq. CHaMgCI OCH3 “W 2) H30“ Page 7 of 15 Points awarded 18. What is the major organic product obtained from the following reaction? 0 H NH2 1. LiA|H4 M NH2 2. H20 3 4 YOH \bN-OH 19. What is the best choice of reagent(s) to achieve the following transformation? ? /\)k MMOH OCH3 3. H20 NaOH, H20 C. LiAIH4; 2. H30+ . H2804 Points awarded Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name February 23, 2011 Part 2. Other questions. “Priced as marked”. For each compound on the left, select the term from the right columns that best describes the functional group in that compound. Place the letter corresponding to your answer in the column to the right of the structure. (3 points each): OH O \ 20 HOHO \ a) nitrile OH O 1’ 21 N/ ‘3 k c) acetal d) enamine CN ' O O O 24 OH Q i) hemiacetal j) lactam b) fi-hydroxyketone f) a,l5-unsaturated ketone h) amide l) B—keto carboxylic acid k) acid chloride Page 9 of15 Points awarded Complete each equation below by drawing the structure of the organic reactant(s) or product(s) that best fit(s) the reaction depicted. Be sure to show stereochemistry correctly, where appropriate. 3.5 points each. 26 1) M9 Br 2) 002 3) I-iao+ -—--------—----> 27 O NaOH, H20 0 r heat Wm... / H \ 28 ‘tm 1) EtOH. H o+ 0\ 2) NaOEt, EtOH / \JLH 4) H30+, heat 29 0 e PPh3 + ———-—-—-——~> 6 Points awarded Organic Chemistry II - X36.B Berkeley Extension EDP#416750 February 23, 2011 30 o o o J) NaOEt q» EtOH EtO OEt MW __E_/i_‘ Name 1' 1) NaOH, H20 2) HCI, H20 3) heat 31 1) NaOEt, EtOH O O 2) 1) NaOH, H20 Br 2) HCI, H20 3) heat +0 ‘ -——-—-———-—-—-—-—-—-—-> ——-—-——-—-—-—-——>~ EtO OEt I 32 O 1) HCI Br Dean—Stark Trap Page 11 of 15 Points awarded 33. Please show a step-by-step mechanism by which cinnamaldehyde is formed from the crossed—aldol reaction of benzaldehyde and acetaldehyde (8 points] 0 O "OH \ H _____.. H +C/EH 34. Please deduce the structures of compounds A—E in the scheme below. (10 points) OH ‘ J (a 2w“ 6 H2CTO4 CBH1OO C7H14O H+, Heat C7H12 / ———-—-———-—-> ———————-> --—--———-> A 2- H+ B C a: 5" x C -—-—--—> ————-————> 2. H30+ D E 4/ o O / ‘0 o o H' / l 1* Points awarded Extra credit: The iodoform test is a common lab test for the presence of a methyl ketone. The test is carried out by treating the putative methyl ketone with excess l2 and hydroxide. Show in a step-by—step process how iodoform (solid, yellow material indicative of a positive test) is produced under these conditions from a methyl ketone (7 points). Also indicate the identity of the other product formed in this process (3 points). 0 i2, "OH PAM .4 I4 CHI3 + other organic product Co 0 A34 9» i+ H' Hp H HI 9 O I 0H C“ A é— R /‘C/\ H 43%” O C) as: ~-—# 12% H’ 14 Q % 1'33) H 0 .4 é: CJW H H o, )Ci (59 Points awarded i» a -———— Herb Organic Chemistry II - X36.B Berkeley Extension EDP#416750 Name February 23, 2011 35. Treating a solution of cis-t-decalone with base causes an isomerization to take place. At equilibrium, the starting material has been converted to approximately 95% trans-t-deaclone and only about 5% cis-1—decalone. Please explain the isomerization — how it occurred and why the equilibrium favors the 0 trans isomer. (8 points) [ / H O /’————A 1" "JL'jacron‘iMj’ H cis—t -deacalone & coil pad 9 I _> z ' o ’1’ H / ' «0 lax Wfl. M $ 6M» , No 36. Please fill in the reagents required rforoea h of the following transformations CN‘AD (15 points) ' O O)<\‘ on 'M Q ~$Tdt I OH HLLrOL" o u b 9*” “‘52 O Co “‘9 so Page 13 of 15 Points awarded ...
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MT1 key (final version) - K27 Part 1: Short answer /...

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