1. Which of the following methods is NOT suitable for the synthesis of Compound X?

(A) 3-methylbut-1-yne

(B) 3-methylbutan-2-ol +

(C) methyl 2-methylpropanoate

(D) acetonitrile

(E) acetyl chloride 

2. How many peaks do you expect to see in the 1H NMR of Compound X (assuming the peaks do not overlap with each other)?(A) 2(B) 3(C) 4(D) 5(E) 6

3. Which of the following would be suitable reagents in Step 1?(A) i) KMnO4, ii) isopropanol, concentrated HCl(B) i) NaBH4, ii) CH3COCl(C) isopropanol, NaH(D) m-chloroperbenzoic acid(E) isopropanol, HCl

4. Which of the following would be the correct 1H NMR of Compound Y?(A) (B)(C) (D)(E) None of the above is correct

5. What is the most likely structure of product Z?(A) (B)(C)(D)(E)

6. Which of the following descriptions about the TLC analysis of Compound G and H is incorrect? (A) If "TLC 1" is a normal phase silica TLC plate, Compound H is more polar than Compound G.(B) If Compound G and H are analyzed again with a reverse phase silica TLC plate in EtOAc:n-hexane (3:2) then "TLC 2" could be the result.(C) "TLC 2" could be the result of running a normal phase silica TLC plate with EtOAc:n-hexane (2:3).(D) The Rf values of both compounds would change if the TLC is run with different ratios of EtOAc and n-hexane.(E) All of the above are incorrect

7. The highest occupied molecular orbital (HOMO) of 1,3,5-hexatriene is:(A)(B) (C) (D)(E)

8. What would be the major product of the following reaction?(A) (B) (C) (D)(E)

9. The reaction in question 8 is classified as a ...(A) [3,3] sigmatropic rearrangement(B) [6π] electrocyclization(C) [4+2] cycloaddition(D) [2+2] cycloaddition(E) [3+3] cycloaddition

10. What would be the major product of the following reaction?(A)(B) (C) (D) (E)

11. Which of the following is/are nonaromatic?(A) 1 and 2(B) 3 and 5(C) 3(D) 4(E) 4 and 5

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