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

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

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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