15. Provide an acceptable name for the compound below.

(A)1,3-diphenyl-3-oxypropane
(B) phenoxyphenylmethane
(C) diphenyl ether
(D)dibenzyl ether
(E) dibenzyl acetal

28. Identify the correct name for the following structure.(A)4-hydroxy-7,N-dimethylcyclohept-6-enamine (B) 5-hydroxy-2,N-dimethylcyclohept-2-enamine (C) 4-methyl-5-(methylamino)cyclohept-3-enol (D)5-methyl-4-(methylamino)cyclohept-5-enol (E) 4-methyl-5-(methylamino)cyclohept-3-en-1-one

16. How would you perform the following transformation? (A)LiAlH4 (B) 1. SOCl2 / 2. LiAlH(O-t-Bu)3 (C) NaBH4 (D)1. DIBAL-H / 2. H2O (E) 1. LiAlH4 / 2. concentrated KMO4

17. What is the best way to perform the transformation shown below?(A) 1. NaCN / 2. H3O+ (B) 1. Mg / 2. CO / 3. H3O+ (C) concentrated KMnO4 (D) 1. NaN3 / 2. H3O+ (E) Both A and B would work

18. Which of the following molecules has a characteristic stretch at 3300 cm-1? (A)(CH3)2CHCO2CH3 (B) (CH3)2CHCH2N(CH3)2 (C) (CH3)3CH (D)(CH3)2CHCH=CH2 (E) (CH3)2CHC≡CH

19. What type of carbon environment does not generate a signal in the DEPT-90 spectrum and gives a positive peak in the DEPT-135 spectrum? (A)methine (B) methylene (C) quaternary (D)methyl (E) carbonyl

20. An NMR spectrometer that operates at a frequency of 60 MHz for 13C NMR spectra, operates at what frequency for 1 H NMR spectra? (A)60 MHz (B) 15 MHz (C) 120 MHz (D)240 MHz (E) 30 MHz

21. If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture? (A)100 (B) 75 (C) 3 (D)50 (E) 25

22. Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut-2-ene, and 3-methylbut-1-ene. When each of these alkenes is subjected to catalytic hydrogenation (H2, Pt), a single product results. Which of the following best describes the structural relationship among these products? (A)The products are diastereomers. (B) The products are identical. (C) The products are constitutional isomers. (D)The products are enantiomers. (E) The products are cis-trans isomers.

23. How many elements of unsaturation are implied by the molecular formula C8H11N? (A)0 (B) 1 (C) 2 (D)3 (E) 4

24. Which of the following terms best describes the stereochemical relationship of the two compounds shown below in Fischer notation? (A)Diastereomers (B) cis/trans – isomers (C) enantiomers (D) constitutional isomers (E) meso - same structure

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