STEREOCHEMISTRY A STUDENT SHOULD BE ABLE TO:

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1 A STUDENT SHOULD BE ABLE TO: STEREOCHEMISTRY 1. Determine the relationship between two given structures (which may be any of the kinds below). Also, define the following terms, and give examples of pairs of molecules having the given relationship. Same compound (completely superimposable) Constitutional isomers (different connectivity of atoms; may include chain, position, and functional group isomers) Stereoisomers (same connectivity of atoms; different orientation in space) Enantiomers (nonsuperimposable mirror images of each other) Diastereomers (stereoisomers that are not mirror images of each other) 2. Define the following, and tell whether or not a given compound or structure fits the description or possesses the feature. Chiral (not superimposable on its mirror image) Achiral (superimposable on its mirror image/has an internal plane of symmetry) Tetrahedral chirality center (stereocenter) Plane of symmetry Optically active (rotates a plane of polarized light) Meso compound (contains two or more chirality centers, but is achiral) 3. Given the structure, write the name, and given the name, draw the structure, of compounds using the (R), (S) system (in addition to the IUPAC system you already know). 4. Understand resolution, the process by which a mixture of enantiomers is separated. 71

2 To best prepare for this module, please work appropriate Skill Builder problems in the textbook. Please use your model kit to prepare for this module. A STUDENT WHO HAS MASTERED THE OBJECTIVES FOR THIS UNIT SHOULD BE ABLE TO SOLVE THE FOLLOWING PROBLEMS AND RELATED ONES: 1.1 State how the two structures in the following pairs are related to each other. They may be constitutional (structural) isomers, enantiomers, diastereomers, or the same compound. 1.2 Identify each of the compounds in question 1.1 above as either chiral or achiral. 72

3 1.3 Answer the following questions for the following sets of four structures. 1) In each set of structures, which of the other three members (II, III, or IV) is not a stereoisomer of the first member of the set? 2) In each set of structures, which two members are enantiomers of one another? 3) What relationship do the two members that are not enantiomers of one another have with the two that are enantiomers of one another? (See 1.1 for possible relationships.) 2.1 Answer the following questions for each of the molecules shown below. 1) How many chirality centers does the molecule contain? 2) Does the molecule possess any internal planes of symmetry? 3) Is the molecule chiral? 4) Is the molecule superimposable on its own mirror image? 5) Is the molecule optically active? 6) Is this a meso compound? 2.2 How many chirality centers does the following structure contain? How many stereoisomers having this structure are theoretically possible? 73

4 2.3 Which of the following compounds has a meso stereoisomer? 3.1 What is the correct priority of these groups with respect to (R), (S) determination in stereochemistry, with highest priority group first? Assume these groups are all bonded to the same chirality center. a) -CH 2 CH 2 Cl -CH 2 OH -CH=CH 2 -C(CH 3 ) 3 b) -CH 2 Br -CHF 2 -OCH 3 -Cl 3.2 Label the following chirality centers as (R) or (S). 3.3 Give the IUPAC name, including the (R) or (S) designations when appropriate, of each of the following compounds. 3.4 Draw the structure of each of the compounds named below. Make sure that your drawing shows a three-dimensional structure in the correct configuration. a) (R)-2-chloropentane b) (3R,4S)-3-ethyl-4-methyl-1-hexyne 74

5 4.1 Draw the product salts that result when a racemic mixture of the amine base reacts with the stereoisomer of the acid shown below. What is the relationship between the product salts? Would you expect their melting points or solubilities to be the same or different? SOLUTIONS TO SAMPLE PROBLEMS: 1.1 a) enantiomers b) same c) enantiomers d) same compound e) diastereomers f) enantiomers g) constitutional isomers h) diastereomers i) same compound j) enantiomers (hint: chairs can flip) k) diastereomers l) diastereomers 1.2 a) both are chiral, b) both achiral, c) both chiral, d) both achiral, e) left structure achiral and right structure chiral, f) both chiral, g) both achiral, h) both achiral, i) both chiral, j) both chiral, k) both chiral, l) both chiral ) 2) 3) a) III II and IV diastereomers b) IV II and III diastereomers 2.1 1) 2) 3) 4) 5) 6) a) 2 no yes no yes no b) 1 no yes no yes no c) 2 yes no yes no yes d) 0 yes no yes no no Tetrahedral chirality centers, 2 6 = 64 possible stereoisomers. However, some of the ring chirality centers cannot be varied independently, so the actual number is less than c 3.1 a) -CH 2 OH > -C(CH 3 ) 3 > -CH=CH 2 > -CH 2 CH 2 Cl b) -Cl > -OCH 3 > -CH 2 Br > -CHF 2 75

6 a) (S)-1-chloro-2,3-dimethylbutane b) (S)-2-bromobutane c) (3R,4S)-3-chloro-4-fluoro-3,4-dimethylhexane d) (3S,4R)-4-chloro-3-methyl-1-pentene 3.4 a) (R)-2-chloropentane b) (3R,4S)-3-ethyl-4-methyl-1-hexyne Note: Your structure may be drawn differently and still be correct 4.1 Diastereomeric salts will form. They will have different properties (such as MP, solubility) that can be used to separate the isomers. 76

7 Name Sixth Drill Test (Sample A) Organic Chemistry 2210D Answer All Questions 1. Consider the molecule at right, and answer each of the questions about it. a) Is it superimposable on its mirror image? b) Is the molecule chiral? c) Does it have a plane of symmetry? d) Is it optically active? e) Is it a meso compound? 2. Give the IUPAC name of each, using (R) or (S) when appropriate. 4. What is the relationship between the structures in each of these pairs? Possible answers are: Same compound, Enantiomers, Diastereomers, and Constitutional (Structural) isomers. 5. a) On the structures in Question 4, identify each compound as chiral or achiral. b) On the structures in Question 4, identify any meso compounds. 77

8 Name Sixth Drill Test (Sample B) Organic Chemistry 2210D Answer All Questions 1. Give the IUPAC name of each compound using (R), (S) designation where appropriate. 2. What is the relationship between the structures in each of the following pairs? Possible answers are: same compound, enantiomers, diastereomers, and constitutional isomers. 3. On the structures in Question 2, identify each compound as chiral or achiral. 4. Draw the structure of a chiral cyclic alkane having a molecular formula of C 5 H

STEREOCHEMISTRY. 2. Define the following, and tell whether or not a given compound or structure fits the description or possesses the feature.

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