hemistry 2321 Test No. 3 Professor M. Pomerantz LD TEST QUESTINS Select the best name for the compounds shown. 1. l 2 3 2 2-chloro-4-ethyl-5-heptyne 6-chloro-4-ethyl-2-heptyne 4-(2-chloropropyl)-2-hexyne 2-chloro-4-(1-propynyl)-2-hexane 6-chloro-4-ethyl-2-heptene 2. 2 3 2 2 2 2-ethyl-5-propyl-3-heptyne 4-ethyl-7-methyl-5-nonyne 2-ethyl-5-propyl-3-heptene 6-propyl-3-methyl-4-octyne 6-ethyl-3-methyl-4-nonyne 3. 3 2 2 3 5,6-dimethyl-3-octyne 3,4-dimethyl-5-octyne 2-sec-butyl-3-hexyne 5-sec-butyl-3-hexyne 2-(1-methylpropyl)-3-hexyne 4. 2 (S)-3-chloro-3-vinyl-1-propyne (R)-3-chloro-1-pentyn-4-ene l (S)-3-chloro-1-pentyn-4-ene (R)-3-chloro-1-penten-4-yne (S)-3-chloro-1-penten-4-yne 5. F (E)-3-flouro-1-hexen-4-yne (R)-3-flouro-1-hexen-4-yne = 2 (Z)-3-flouro-1-hexen-4-yne cis-3-flouro-1-hexen-4-yne (S)-3-flouro-1-hexen-4-yne What is the major organic product from the following reactions 5a. 3 excess ether 3 2 2 3 2 3 2 2 3 3
Page 2 - hemistry 2321 - ld Test Questions - Test No. 3 6. 2 3 Li N 3 (l) 2 2 2 2 2 2 2 2 A mixture of d and 2 2 6a. B 3 TF 3 2 3 2 2 3 2 2 2 2 2 3 2 3 2 3 2 7. 2 2 2 2 gs 4 2 S 4 2 2 2 2 2 2 8. NaN 2 N 3 (l) 2 2 2 2 2 2 3 2 2 N 2 No reaction occurs 9. 3 + 2 + + + 2 + 2
Page 3 - hemistry 2321 - ld Test Questions - Test No. 3 10. (E)-2-butene + l 2 l 4 l l only l l only l l only an equal mixture of a and b an equal mixture of a and c 11. 6 5 6 5 2 K / 2 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 6 5 What reagent(s) can be used to carry out the conversions shown 12. 3 1) B 3 TF; 2) 2 2 / 1) s 4 ; 2) NaS 3 gs 4, 2 S 4, 2 2 / Lindlar's catalyst 13. 2 Li / N 3 (l) 1) B 3 TF; 2) 2 2 / 2 / Lindlar's catalyst 1) 2 / Pt; 2) 1) 2 / l 4 ; 3) K / 2 5 1) 2 / l 4 ; 2) NaN 2 / N 3 (l) 14. 3 3 2 1) NaN 2 / N 3 (l); 2) 2 Na 2 15. 1) NaN 2 / N 3 (l); 2) l 2 Either a or b 1) NaN 2 / N 3 (l); 2) 6 5 6 5 2 2 Li / N 3 (l) 1) B 2 / Lindlar's catalyst 3 -TF; 2) 2 2 / / 2 Both a and b are correct 2 Pd / 16. 2 cold, dilute KMn 4 1) s 4 ; 2) NaS 3 2 / Lindlar's catalyst 2 2 1) B 3 -TF; 2) 2 2 / / 2 gs 4 / 2 S 4 / 2
Page 4 - hemistry 2321 - ld Test Questions - Test No. 3 17. Which of the following reactions will not occur A) B) NaN 2 N 3 (l) NaN 2 N 3 (l) ( ) 3 I ( ) 3 ) D) NaN 2 N 3 (l) NaN 2 N 3 (l) 2 2 l l A only A, B and D B only None of them will occur D only 18. Which of the following has the R absolute configuration 2 2 2 a and c a, b and c 19. Which of the following molecules is not chiral l 2 All are chiral 20. Which of the following has the R absolute configuration 2 3 2 5 2 3 A B 3 A All of them B A and 21. Which of the following compound(s) is (ar meso l l l l l l A B A A, B and B B and l
Page 5 - hemistry 2321 - ld Test Questions - Test No. 3 22. Which of the following is the enantiomer of the structure below 2 5 2 5 3 2 2 5 5 2 5 3 2 5 23. Which of the following is a diastereomer of the structure below 3 3 24. Which of the following shows a pair of enantiomers and 3 and 3 both b and c and 3 and 3 25. Which of the following compounds is a diastereomer of the structure shown below None of them
Page 6 - hemistry 2321 - ld Test Questions - Test No. 3 26. Which of the following compounds is not a chiral molecule 3 all are chiral 3 Show step-by-step (include reagents and solvents/conditions where crucial) how you would convert the compound given to the product shown. You can use any stable organic molecules containing NE or TW carbon atoms in addition to the starting compound, any inorganic reagents and any solvents. Write clearly and TINK!!! 27. 3 2 2 28. 2 2 3 2 2 29. 3 3 meso only (TINK!!!) 30. 2 31. 3 3 2 2 2 32. 2 2 3 cis only