CHM247 Tutorial #3 (slides can be accessed here)

Question #1 – Draw Structures a)1-chloro-8,8-dimethyl-2,5-decadiyne b) (E, 5R)-5,8-dibromo-4,6,7-trimethyl-6-octen-1-yne

“Predict the products of 4-octyne reacting with the following reagents” a)HgSO 4, H 2 O, H 2 SO 4 b)Na, NH 3 (l) c)2 equivalents of HCl d)H 2, Lindlar catalyst e)KMnO 4, H 3 O +, Heat Question #2 - Reactions

“Predict the products of 4-octyne reacting with the following reagents” a)HgSO 4, H 2 O, H 2 SO 4 b)Na, NH 3 (l) c)2 equivalents of HCl d)H 2, Lindlar catalyst e)KMnO 4, H 3 O +, Heat Question #2 - Reactions

“Predict the products of 4-octyne reacting with the following reagents” a)HgSO 4, H 2 O, H 2 SO 4 b)Na, NH 3 (l) c)2 equivalents of HCl d)H 2, Lindlar catalyst e)KMnO 4, H 3 O +, Heat Question #2 - Reactions

Question #3 - Synthesis “Show how you might synthesize each of the following compounds, using ethyne as your starting material and using compounds that contain no more than 5 carbon atoms” a)2-octyne b)(E)-3-hexene c)2-methyloctane  Always look for the starting material in the product  Use a disconnection strategy

Question #3 – Synthesis (answers) Reactions 1 and 2 are interchangable

Question #3 – Synthesis (answers) Reactions 1 and 2 are interchangable

Look like coupling partners Question #4 a)C 7 H 12 O 2 IR: 3300 – 3600, 2250 cm -1 1 H NMR: 5.2 (triplet, 1H), 2.9 (septet, 1H), 2.4 (singlet, 2H), 2.3 (doublet, 2H), 1.2 (doublet, 6H) 1 – find D.O.U. 2 – look for possible functional groups in the IR 3300 – 3600cm -1  Alcohol 2250cm -1  could be an Alkyne 3 – start to piece together fragments and fit them with the NMR data Isopropyl