8. Which of the following substituent has the highest priority according to the Cahn-Ingold-Prelog system? 

(A) –COOH
(B) –CHO
(C) –CH₂OH
(D) –CH₃
(E) -H

9. What is the IUPAC name of the expected major product formed upon reaction of HCl with 3-methyl-1-butene?(A) 1-Chloro-2-methylbutane (B) 1-Chloro-3-methylbutane (C) 2-Chloro-2-methylbutane (D) 2-Chloro-3-methylbutane (E) 1-Chloropentane

10. Which sequence correctly ranks the following substrates in order of increasing reactivity in an SN1 reaction?  (A) 3 < 2 < 1 (B) 2 < 3 < 1 (C) 2 < 1 < 3 (D) 1 < 3 < 2 (E) 1 < 2 < 3

11. A pure sample of (S)-phenylalanine has a specific rotation of +70o . A mixture of the two enantiomers of phenylalanine gives a specific rotation of -7.0o . What are the percentages of the S and R enantiomers in the mixture? (A) 75 % S, 25 % R (B) 65 % S, 35 % R (C) 55 % S, 45 % R (D) 45 % S, 55 % R (E) 35 % S, 65 % R

12. Predict the major product when pyridine is treated with a mixture of nitric acid and sulfuric acid (A) 2-nitropyridine (B) 3-nitropyridine (C) 4-nitropyridine (D) 2,3-dinitropyridine (E) 2,4-dinitropyridine

13. Predict the product(s) for the following reaction.Diethylheptanedioate ?(A) I (B) II (C) III (D) IV (E) V

14. Which molecular formula is consistent with the following mass spectrum data?   at m/z= 84, relative height=10.0%  at m/z= 85, relative height=0.56% (A) C5H10O (B) C5H8O (C) C5H24 (D) C6H12 (E) C4H6O2

15. Which sequence correctly ranks the following dienes in order of increasing reactivity in the Diels-Alder reaction?  (A) 3 < 2 < 1 (B) 2 < 3 < 1 (C) 2 < 1 < 3 (D) 1 < 3 < 2 (E) 1 < 2 < 3 .

16. Rank the following compounds in increasing order of reactivity in the intramolecular displacement of p-bromophenolate to form a cyclic anhydride. (A) A < B < C (B) B < A < C (C) C < A < B (D) B < C < A (E) None of above

17. Which of the following undergoes solvolysis in water more rapidly?   (A) I (B) II (C) III (D) I and II (E) all of the above

18. Grignard reagents react with oxirane (ethylene oxide) to form 1o -alcohols but can be prepared in tetrahydrofuran solvent. Why is this difference in behavior observed? (A) Steric hindrance in the case of tetrahydrofuran precludes reaction with the Grignard. (B) There is a better leaving group in the oxirane molecule. (C) The oxirane ring is the more highly strained. (D) It is easier to obtain tetrahydrofuran in anhydrous condition. (E) Oxirane is a cyclic ether, while tetrahydrofuran is a hydrocarbon.

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