CHAPTER 5: STEREOISOMERS
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1 APTER 5: STEREISMERS SIMPLE STEREISMERS NSTITUTINAL ISMERS VERSUS STEREISMERS A constitutional isomer A stereoisomer Page 1
2 IRALITY (ANDEDNESS) hiral object: Achiral object: Are these objects chiral or achiral? golf club IRAL MLEULES F F A B Page 2
3 AIRAL MLEULES A B SPTTING IRALITY QUIK TRIK MIRRR PLANES F SYMMETRY F 3 3 Page 3
4 IRAL ENTERS AND ENANTIMERS Which of these compounds has an enantiomer? If it does, draw the enantiomer Find the chiral center in the structure below, then draw the enantiomer. Prozac (antidepressant) is one of the enantiomers. N 3 F 3 Page 4
5 IRAL INTERATINS BIATIVITY IRAL-IRAL INTERATINS Page 5
6 TP 10 PRESRIPTIN DRUGS By number of monthly prescriptions in the USA, May 2015 data. #1: Synthroid (levothyroxine) (synthetic thyroid medicine) 21.5 million #2: restor (rosuvastatin) (statin for cardiovascular disease) 21.4 million #3: Ventolin (albuterol) (asthma inhalers) 18.2 million #4: Nexium (esomeprazole) (ulcers, gastric reflux) 15.2 million #5: Advair (fluticasone) (asthma, pulmonary disease) 13.7 million #6: Lantus (insulin glargine) (controlling blood sugar, diabetes) 10.9 million #7: Vyvanse (lisdexamfetamine) (treating ADD and binge eating) 10.4 million #8: Lyrica (pregabalin) (treating epilepsy, anxiety, pain) 10.0 million #9: Spiriva (tiotropium) (chronic bronchitis & emphysema) 9.6 million #10: Januvia (sitagliptin) (anti-diabetic) 9.1 million Page 6
7 Page 7 MULTIPLE IRAL ENTERS IRAL ENTERS AND MAXIMUM NUMBER F ISMERS D-allose D-mannose D-galactose D-altrose D-gulose D-talose L-allose L-mannose L-galactose L-altrose L-gulose L-talose D-glucose D-idose L-glucose L-idose
8 ENANTIMERS A B DIASTEREMERS A B 3 Draw the enantiomer Draw a diastereomer (many answers) Page 8
9 MES MPUNDS Are these meso compounds or not? 3 3 Page 9
10 R,S NMENLATURE METD 1. Rank the groups around the chiral center from 1 to 4, using atomic number (# protons). The higher the atomic number the higher the rank. Atom Atomic # Rank F F 2. Position the lowest ranking group (#4) away from you. Follow the direction of the groups from 1 to 2 to MRE INVLVED RULES WEN ATMS ARE TE SAME Move down the chain one atom at a time until the first point of difference. Page 10
11 RINGS Treat each half of the ring as separate groups. * * IF #4 IS TWARD YU MULTIPLE BNDS Treat the atoms like they re duplicated, as many times as there are multiple bonds. Page 11
12 EXAMPLES The active ingredient in Aleve (pain relief, anti-inflammatory) is the (S) enantiomer. Which compound below is the active ingredient in Aleve? 3 3 Na Na 3 3 Fully name this compound, including R,S naming. PYSIAL PRPERTIES DENSITY, SLUBILITY, MELTING PINT, BILING PINT, ET. Mp ( ) Density (g/ml) What would the G spectrum of a sample containing these two compounds look like? Page 12
13 PTIAL ATIVITY PLARIMETRY SIGN F PTIAL RTATIN Page 13
14 ENANTIMERS NEW TERMS 1) RAEMI MIXTURE 2) ENANTIMERI EXESS Draw a mixture that represents 80 ee Page 14
![A B a) [a ] = +5.8 b) [a ] = -5.8 c) [a ] = 0 d) None of these 4.](/docs-images/96/128704451/images/15-1.jpg "Given the physical properties of compound X (fabricated), what should be the physical properties of compound Y? X b.p. = 193, [a ] = -53 Y Boiling point of Y: a) b.p. = 193 b) b.")
15 PRBLEMS 1. What is the relationship between each set of compounds? Are they constitutional isomers, enantiomers, diastereomers, identical, or not related (not isomers)? 3 2. Which of the following compounds are chiral? 3. The optical rotation of compound A is [a ] = +5.8 (fabricated). What should be the optical rotation of compound B? A B a) [a ] = +5.8 b) [a ] = -5.8 c) [a ] = 0 d) None of these 4. Given the physical properties of compound X (fabricated), what should be the physical properties of compound Y? X b.p. = 193, [a ] = -53 Y Boiling point of Y: a) b.p. = 193 b) b.p. = 0 c) None of these. ptical activity of Y: a) [a ] = +53 b) [a ] = -53 c) [a ] = 0 d) None of these. Page 15
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