3. For ONE of the following molecules, redraw the molecule and indicate on your drawing: CI NH (1) all the n-bonds (circle these). (ii) any atoms that are chiral (stereogenic) (mark with an asterisk * AND a number 1, 2, 3, etc.) (iii) the absolute configuration of any chiral (stereogenic) centres marked in (ii) above.
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- 4. - Determine the structural relationship between the compounds in each of the pairs that follow. They may be unrelated, identical (the same compound), constitutional isomers, diastereoisomers, enantiomers? - Identify the optically active (chiral) compounds and any meso compounds. - Assign a configuration (R or S) to all stereocenters. - Name all compounds so that the name reflects the structure unambiguously. a) b) c) d) e) f) H- HO- CHO H3C -NH₂ H- -H H- CH2OH H CH3 CH3 H Ph H CH3 H H CI Ph H H CI CH3 CH₂OH -OH -NH₂ CI H H CI & t OH CHO H3C H OH O-CH3 oma O-CH3 H3C OH3. The structure of (L)-menthol is shown below. How many chiral centers does this molecule possess? Starting from the top of the molecule, and moving in a clockwise direction, identify the absolute configuration (R or S) of each of these chiral centers.Q2: If you think you know your definitions, try this difficult problem. (a) Draw all the stereoisomers of 2,3.4-tribromonentane, (Using Fischer projections may helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (S). (c) In the meso structures, show how C3 is pot asymmetric, nor is it a chiral center, Yetn stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.
- (a) (1R,2R)-1,2-dibromocyclohexane, star (*) each chiral center.(a) Draw all the stereoisomers of 2,3,4-tribromopentane. (Using Fischer projections may be Q2: If you think you know your definitions, try this difficult problem. helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (5). (c) In the meso structures, show how C3 is pot asymmetric, nor is it a chiral center, yet it is a stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.(a) Draw all the stereoisomers of 2,3,4-tribromopentane. (Using Fischer projections may be Q2: If you think you know your definitions, try this difficult problem. helpful.) You should find two meso structures and one pair of enantiomers. (b) Star (*) the asymmetric carbon atoms, and label each as (R) or (5). tej in the meso structures, show how C3 is not asymmetric, nor is it a chiral center, yet it is a stereocenter. (d) In the enantiomers, show how C3 is not a stereocenter.
- Draw mirror images for these molecules. Are they different from the original molecule? (a) (b) • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Include H atoms at chiral centers only. • Use the "flat" representation of rings in your drawing where appropriate. ● HO ||||| O different O the same Sn [F ? ChemDoodleⓇassign the stereochemical configuration of the selected tetrahedral carbon chiral centers (R, S or N (not a chiral center)) and the alkene (E, Z or N (not a stereocenter)) that are indicated by the arrows (note that you do not have to assign the configuration of every chiral center in the molecule). If the atom in question is not a chiral center or is not a stereocenter circle N for neither.1.) Name this molecule and identify and assign a configuration if there are chiral centers. a) (25, TR)-9-chloro-2,7-diethyl nonane b.) (25, 6R,7R) - 2-chloro-6,7-diethyl-8-methylnonane c.) (2R, 65, 75)-2-chloro- 6,7-diethyl - 8-methyl nonane d.) (25, 65, 75)-9-chloro-3,4-diethyl octane
- Question 4: a) Using Cahn-Ingold-Prelog (CIP) rules assign the absolute configuration of all the stereocenters in the molecule below, then indicate whether or not is chiral, if achiral, show the element of symmetry. b) Draw out all possible diastereomers of this molecule c) Draw out all the enantiomers for the molecule below in addition to the diastereomers you drew in part (b). Indicate which of the molecules on your page are meso compounds. НО. HO H H O 4 H OH OH3. Determine whether the following statements are true or false. Completely fill in the circle in front of your chosen answer. (a) A compound with a plane of symmetry must be achiral. (b) A compound with two or more stereocenters must be chiral. (a) O True O False True O False(a) Identify type of molecules either chiral, achiral, or meso for each compound shown below and (b) Indicate the number of chiral centers in each molecule.