The following 30 point quiz contains 20 multiple choice questions valued at 1.5 points/question, and an unknown analysis question valued at 6 points.

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Reginald Lambert
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1 Chemistry 262 Quiz 2 Spring 2018 Principally Chapters 17, 20, and 21 ame: KEY The following 30 point quiz contains 20 multiple choice questions valued at 1.5 points/question, and an unknown analysis question valued at 6 points. 1. Which of the following conditions will lead to 3-bromocyclohexene as the principal product? a. Cyclohexene + H + peroxide b. Cyclohexene + BS/C4 + peroxide c. omobenzene + a 0 d. All of the above e. one of the above 2. When toluene is reacted in turn with 1) excess 2 while irradiated with UV light, followed by 2) 2 + Fe3, the principal product is C 3 C 3 C 3 I II III e. A mixture of III &

2 3. What is the most likely product resulting from the treatment of 1,4- cyclohexadiene with BS/C4/AIB? a. 3-bromo-1,4-cyclohexadiene b. 3,6-dibromo-1,4-cyclohexadiene c. 5-bromo-1,3-cyclohexadiene d. 3,4,5-tribromo-1-cyclohexene e. 3,3,6,6-tetrabromo-1,4-cyclohexadiene 4. What is the name of the product formed when para-methyl styrene is subjected to aggressive alkaline KMn4 conditions, and subjected to acidic conditions upon work-up? a. para-methyl benzoic acid b. para-vinyl benzoic acid c. para-methanoyl benzoic acid d. Terephthalic acid e. Adipic acid 5. Which of the following will not result in the formation of hexanoic acid? a. zonolysis of cyclohexene, followed by oxidative (H22) work up b. Treatment of n-hexanol with a2cr27 in H2S4 c. Heating ethyl caproate with ah, followed by H work-up d. Treating hexyl bromide with Mg 0 in THF, followed by C2 (s), followed by H work up e. /A; all of the above yield hexanoic acid

3 6. What is the common name for the following compound? a. Succinic acid b. Glutaric acid c. Maleic acid d. Fumaric acid e. Tartaric acid 7. What is the preferred IUPAC name for phthalic acid? a. Benzene-1,2-dicarboxylic acid b. Benzene-1,3-dicarboxylic acid c. Benzene-1,4-dicarboxylic acid d. ortho-toluic acd e. para-toluic acid 8. Which of the following is the correct structure for glutaric acid? H I H H II H H H III H H e. one of the above

4 9. The structure corresponding to 2-methylbutyl ethanoate is? I II III V 10. Which of the following structures is -benzyl--propyl-2,3- dimethylbutanamide? H I II III V

5 11. Which of the following would be the weakest acid? a. Benzoic acid b. 4-itrobenzoic acid c. 4-Methylbenzoic acid d. 4-Methoxybenzoic acid e. 4-Fluorobenzoic acid 12. What is the initial reactant in the following reaction sequence?? i. LAH, Et 2 ii. H 2 P 3 i. Mg, Et 2 ii. C 2 iii. H 3 + C 2 H C 2 H C 2 H C 2 H I II III V 13. What is the principal outcome of the following reaction sequence? C 6 H 5 ac i. excess LAH, Et 2 ii. H 2? a. C 6H 5CH 2CH 2C 2H b. C 6H 5CH 2CH 2H 2 c. C 6H 5CH 2CH(CH 3)C d. C 6H 5CH 2CH=H e. C 6H 5CH 2H 2

6 14. The relative reactivity of acyl compounds toward nucleophilic acyl additionelimination is a. Amide > ester > acid anhydride > acyl chloride b. Acyl chloride > ester > acid anhydride > amide c. Ester > acyl chloride > acid anhydride > amide d. Acyl chloride > acid anhydride > ester > amide e. Acid anhydride > acyl chloride > ester > amide 15. Please provide the structure for the product formed when butanoic acid is treated with (a) S2, followed by (b) isopropyl alcohol/pyridine, followed by diethyl amine under reflux conditions Structure should correspond to,-diethylbutanamide 16. Alkaline hydrolysis of an ester involves initial attack by hydroxide ion on the carbonyl carbon. The presence of substituents on the aromatic ring of ethyl benzoate may be expected to increase/decrease the rate of hydrolysis of this ester. In what order should the five substituents below be arranged to represent the decreasing order of the rates of hydrolysis when these substituents are present in the para- position of the aromatic ring in ethyl benzoate? a. -2 > -H > - > -CH3 > -CH3 b. -2 > - > -H > -CH3 > -CH3 c. -CH3 > -CH3 > - > -H > -2 d. - > -2 > -H > -CH3 > -CH3 e. -H > - > -CH3 > -CH3 > -2

7 17. Which of the following is mysterious product Z? 1 p-chlorotoluene i. KMn 4, H, heat ii. H 3 + iii. S 2 iv. CH 3 CH 2 H, base Z I II III V 18. A nitrile is prepared from the corresponding primary amide by reaction with which of these? a. H b. 2 c. P410 d. H e. Al3 1 In step 4, base refers to a weak nitrogenous base, preferably hindered

8 19. Which of the following corresponds to product M? i. H 3, H 2 ii. dilute H, cold M H H H H 2 H H 2 I II III H H 2 V 20. What is the major product of the following reaction sequence? C 2 H i. P 5 ii. H 3 iii. P 4 H 10, heat? a. CH3CH2CH2H2 b. CH3CH2CH2 c. CH3CH2CHCCH2CH3 d. CH3CH2C e. CH3CH2C - H4 +

The following homework assignment contains 26 questions valued at ¾ point/question

Chemistry 262 Homework 2: Principally Chapters 17, 20, and 21 ut: 04/27/18 Due: 05/04/18 The following homework assignment contains 26 questions valued at ¾ point/question Name: KEY 1. What would be the