8. List of the following compounds in order of increasing reactivity in a S_N1 reaction. (i) Mel (ii) nBuBr (iii) tBul (iv) iBuBr (v) iBul
(A)i＜ii＜v＜iv＜iii
(B)i＜ii＜iv＜v＜iii
(C) iii＜v＜iv＜ii＜i
(D)iii＜iv＜v＜ii＜i
(E) iii＜i＜iv＜ii＜v

1.Which of these dienes is the most reactive in the Diels-Alder reaction? (A) 1,3-Butadiene (B) 1,4-Pentadiene (C) 2,3,-Dimethyl-1,3-butadiene (D) 1,2-Butadiene (E) 1,4-Cyclohexadiene

2.Which of the following is not true concerning the strength of a nucleophile? (A) Nucleophilicity may not parallel basicity. (B) Negatively charged nucleophiles are always more reactive than their conjugate acids. (C) The greater the strength of a nucleophile, the faster an Sn2 reaction will occur. (D) Strong bases are always good nucleophiles (E) None of these answer choices are correct.

3.Why is sodium methoxide not used in the Claisen condensation of ethyl acetate? (A) The methoxide is a weaker base than the ethoxide which is used. (B) sodium methoxide is more difficult to prepare than sodium ethoxide. (C) The methoxide would abstract a proton from the ethyl group of the ester. (D) Use of sodium methoxide would result in transesterification. (E) sodium methoxide can be used as well as sodium ethoxide.

4. Which of these is not a reversible process? (A) Base-promoted ester hydrolysis (C) Aldol addition (E) Acetal formation (B) Acid-catalyzed ester hydrolysis (D) Claisen condensation

5. A compound has the molecular formula, C6H12O2. Its IR spectrum shows a strong absorption band near 1740 cm -1； its 1H NMR spectrum consists of two singlets, at δ 1.2 and 3.6 ppm. The most likely structure for this compound is: (A) Isopropyl propionate (B) Propyl propionate (C) Ethyl isobutyrate (D) tert-Butyl acetate (E) Methyl pivalate

6. Which of the following terms correctly describes these compounds listed below?(A) conformational isomers (D) constitutional isomers H (B) not isomers (E) enantiomers (C) stereoisomers

7.Which of the following predictions of δ value and splitting pattern of the labeled protons in 1H NMR (CDCI3) is true? (A) Ha (2.5 ppm, triplet) (B) Hb (3.1 ppm, triplet of triplet)(C) Hc (3.1 ppm, triplet of triplet)(D) Hd (2.2 ppm, triplet of doublet) (E) He (2.0 ppm, singlet)  

9.Which of the following compound is aromatic? Me B B. (A)(B)(C)(D)(E)

10. Which of the following amine can be resolved into enantiomers? (A) (B)(C) (D)(E)

11. At some temperatures, the relative reactivities of 3°, 2° and 1°alkane hydrogens in free radical chlorination are in the ratio of 5:3:1. What would be the expected percentages of monochlorination of isopentane produced? (i) 2-chloro-2-methylbutane, (ii) combined 1-chloro-2- methylbutane and 1-chloro-3-methylbutane, and (iii) 2-chloro-3-methylbutane. (A) 10% (i), 75% (ii), 15% (iii) (B)25% (i),45% (ii),30% (iii) (C) 29% (i), 44% (ii),18% (iii) (D)30% (i),35%(ii),35% (iii) (E) 36% (i), 43% (ii), 21% (iii)

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