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- Cyclohex-2-enone has two protons on its carbon–carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C = O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.Cyclohex-2-enone has two protons on its carbon-carbon double bond (labeled Ha and Hb) and two protons on the carbon adjacent to the double bond (labeled Hc). (a) If Jab = 11 Hz and Jbc = 4 Hz, sketch the splitting pattern observed for each proton on the sp2 hybridized carbons. (b) Despite the fact that Ha is located adjacent to an electron-withdrawing C=O, its absorption occurs upfield from the signal due to Hb (6.0 vs. 7.0 ppm). Offer an explanation.For each compound given below, determine whether tthe two labeled hydrogens (a and b) are homotopic, enantiotopic, and diastereotopic.
- At room temperature, the 'H NMR spectrum of all-cis-1,2,3,4,5,6-cyclohexanehexacarboxylic acid exhibits two signals for the H atoms directly bonded to the ring. Explain why. Hint: Draw its chair conformation explicitly. CO,H HO,C .CO2H HO,C* *CO2H CO,H8. Two structures of Lipitor (a drug used to lower cholesterol) are shown below. (a) Determine the absolute configuration of each indicated stereocenter. Fill in the correct circle. (b) Determine if the two structures are the same compound or stereoisomers. Fill in the correct circle. (a) НО. Carbon a HO O OH Carbon a: OR OS Carbon b H N Carbon b: R OS of H Carbon c: OR OS OH OH Carbon c F Carbon d: R OS OH Carbon d (b) The two structures are: O the same compound O stereoisomersA sulfonium ion (R3S+) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an R or S) is a stereogenic center if three different alkyl groups are bonded to sulfur because sulfur is surrounded by four different groups, including its lone pair. In assigning an designation to sulfur, the lone pair is always assigned the lowest priority (4). SAM, S -adenosylmethionine, is a biologically active sulfonium ion that we will learn about in Section 7.16. Locate all the stereogenic centers in SAM, and assign an R,S designation to each center.
- • Consider the following compounds. Assign the R or S configuration to each stereogenic center (add answers onto structures): CH,CH, OCH3 CH3 CH,CH3 сно H;CO,C NH2 co,H 18 Assign the absolute configuration at the stereogenic centre C3 of compound Y. OH Compound Y Assign the absolute configuration at the stereogenic centre C2 of compound Y. Br HO 1 CF3 bund Y Assign the absolute configuration at the stereogenic centre(s) C2 abd C3 of compound Y. HO, HO, 20 Compound Y רUse Apendix C or Figure 18.9 to determine whether Kc > 1 or Kc < 1 for each reaction. (a) H2SO3 + NH3 HSO3- + NH4+ Kc < 1 or Kc > 1 (b) HCN + HCO3- H2CO3 + CN - Kc < 1 or Kc > 1Label or circle CARBON chirality centers for both structures below and determine the maximum number of stereoisometric forms: cortisone (steroid used for anti-allergen creams) HO .OH HO Boye # of Stereoisomers Possible: histidine (one of the 20 amino acids) HO NH₂ # of Stereoisomers Possible:
- How to ID and assign each stereocenter (using cahn, ingold) R, S system.In an IR spectrum, the C-0 stretch for an alcohol (ROH) or an ether (ROR) appears near 1050 cm¯1, but for a carboxylic acid (RCO,H) or an ester (RCO,R), the C-0 stretch appears near 1250 cm-1. Explain why. -1050 cm-1 -1050 cm-1 -1250 cm-1 -1250 cm-1 R R R RI need help in identifying its stereocenters and assigning R or S to it.