MT1 key - Part 1: Short answer / Multiple Choice (3 points)...

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Unformatted text preview: Part 1: Short answer / Multiple Choice (3 points) each. 1. What is the lUPAC name of the following compound? 0 a. (S)—3,4,4-trimethylpentanal " I Pk (19 (R)-3,4,4-trimethylpentanal c. (R)—3-tert-butyl—3-methylpropanel \ ’2. P15 d. (R)-3-tert—butylbutanal 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 W 22:) (CH3)2CHBr (CH3)2CHCH2Br CH3CH2CHzBr CH3CHzBl' o /0 W0 /“\ WAD YV 1 2 3 4 a. only 1 @ only 3 c. only 1 and 3 d. only 2 and 4 Points awarded Chemistry 227 Contra Costa College Name March 3, 2011 3. What is the correct assignment of the names of the following functional groups? 0'4st X F53. may 1 2 3 4 a. 1 acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal b. acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol enol; 2 = hydrate; 3 = hemiacetal; 4 = enol Q0 AA 4. What is the major organic product obtained from the following reaction? 1 st04 h 2 A O OH O OH HO 6 4 QOH (01m 5. What is the relationship between the following two structures? :0: . : M@ M a, tautomers b. constitutional isomers, but not tautomers esonance structures d. stereoisomers Page 3 of 12 Points awarded 6. Which compound is the most acidic/has the lowest pKa? O O O O 7. Which of the following has the highest boiling point? a. hexane b. 1-pentanol c. pentanal d. butanoic acid 8. Which of the following is the most soluble in water? @acetic acid . pentanol c. butanoic acid d. pentanal 9. What is the approximate pKa value of butanoic acid? a. -2 @5 c. 15 d. 35 Points awarded Chemistry 227 Contra Costa College Name March 3, 2011 10. What is the major organic product obtained from the following reaction? 0 o 1. LiAIH4 W 2. H30+ —----> OH OH 0 OH OH H 11. What is the major organic product obtained from the following reaction? 0 CH30H20H 0 OH ' ‘ /\ H2804 ° 12. What is the major organic product obtained from the following reaction? ——..————>. OH 0 OH \[/\Cl 5002 1 2 o o \HLO CI \HKCI a o Page 5 of 12 Points awarded 13. What is the major organic product obtained from the following reaction? 0 k 0 J\ AN /U\N o o _ H A k 1 2 A / 0 u w o o ANA iN/[K 3 4 14. What is the major organic product obtained from the following reaction? 0 O N excess H20 YO? cat. st04 ® 2 \ NH YNHz 4 3 15. What is the major organic product obtained from the following reaction? 0 OH 0 OH 1) 2 eq. CH3MgCI 00H3 —--—-> OCH 2) H3O” 3 1 2 9 4 Points awarded Chemistry 227 Contra Costa College Name March 3, 2011 16. What is the major organic product obtained from the following reaction? 0 1 2 H NH; 1. LiA|H4 —----—)v NH2 2. H20 3 4 YOH VN-OH 17. What is the electrophile in the reaction of benzene with a mixture of nitric acid and sulfuric acid? a. HONO b. NO” of .benzene 18. Which of the following substituents is ortho/para directing and deactivating in electrophilic aromatic substitution reactions? . OH do! 0. CH3 d. N02 19. What is the major organic product obtained from the following reaction? OH heat i5 0 H, O Page 7 of 12 Points awarded 0 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. (2 points each): OH O 20 H0 9 a) nitrile HO \ OH O N b) fi—hydroxyketone r 3 \{\ c) acetal d) enamine g) lactone h) amide 21 / f) a,B-unsaturated ketone CN O O O 24 OH i) hemiacetal j) lactam l) B-keto carboxylic acid k) acid chloride Points awarded Chemistry 227 Contra Costa College Name March 3, 2011 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 points each) 26 1) Mg Br 2) 002 0‘ O/\/ 3) H30+ GM‘ 01‘" WV 27 «1%» x 28 1) NaOEt, EtOH o o 2) 1) NaOH, H20 0 Br 2) H01, H20 J 3) heat H o —~——————————————> —-———————+- EtO OEt Page 9 of 12 Points awarded 29 o 1) HCI OH Ho/V 1) Mg H01, H20 ——-“—————+ —_—> M Br Dean-Stark 2) O \ Trap 30. Please deduce the structures of compounds A-E in the scheme below. (11 points) OH H20r04 CGH1OO C7H14O H+, Heat C7H12 _______..—_*_>—___., A 2. H+ B C 8‘: 53 53 -———> ——> 2. H3O+ D E \e 0 \ O (O f ow Hz Points awarded ...
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MT1 key - Part 1: Short answer / Multiple Choice (3 points)...

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