(a)
Interpretation: The maximum number of stereoisomers that could exist for 1,2-cyclohexanediol needs to be determined, if the formula is 2n ( n = number of stereocenters).
Concept Introduction: Organic compounds are the compounds which are mainly composed C and H atoms. The branch of chemistry that deals with preparation, reactions, and properties of organic compounds. The compounds with same molecular formula and different structural formula are called as isomers. Isomers can be classified as constitutional isomers and stereoisomers.
Constitutional isomers can be defined as the pair of molecules with the same molecular formula but different structural formula. Stereoisomers have same molecular and structural formula but they have different arrangement of atoms in the three-dimensional space.
Optical isomers are type of stereoisomers which have same molecular and structural formula but they have different arrangement of atoms in the three-dimensional space. The essential condition for a molecule to be optical isomer is the presence of chiral carbon atom.
(b)
Interpretation: The reason of three stereoisomers of 1, 2-cyclohexanediol rather than calculated value 4 needs to be explained.
Concept Introduction: Organic compounds are the compounds which are mainly composed C and H atoms. The branch of chemistry that deals with preparation, reactions, and properties of organic compounds. The compounds with same molecular formula and different structural formula are called as isomers. Isomers can be classified as constitutional isomers and stereoisomers.
Constitutional isomers can be defined as the pair of molecules with the same molecular formula but different structural formula. Stereoisomers have same molecular and structural formula but they have different arrangement of atoms in the three-dimensional space.
Optical isomers are type of stereoisomers which have same molecular and structural formula but they have different arrangement of atoms in the three-dimensional space. The essential condition for a molecule to be optical isomer is the presence of chiral carbon atom.
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EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
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- 4. Consider the species 2,3-butanediol, whose structural formula is: но OH 2,3-butanediol H3C CH3 a) There are three distinct, pure, configurational stereoisomers of 2,3-butanediol, all of which have the same structural formula above. Using any unambiguous notation, draw the three different stereoisomers in the boxes below. (The boxes have been arbitrarily labeled A, B, and C.) A В b) By circling the appropriate terms below, indicate whether each of the three species you drew above is chiral or achiral. A: chiral achiral B: chiral achiral С: chiral achiral c) Two of the above species have the same melting point (19°C). The other species has a different melting point (34°C). Circle the letter of the species which has a melting point of 34°C: А В с What characteristic of the other two stereoisomers causes them to share the same melting point (19°C)?arrow_forwardBuild models of cis-1,2-dichlorocyclohexane and trans-1,2-dichlorocyclohexane. Build their mirror images. Notice that the mirror images of the cis stereoisomers are superimposable but the mirror images of the trans stereoisomers are not superimposable.arrow_forwardH ÇI CH3-C-COOH он CH3-C-CH2Br 1. ČI a b 81. Consider the structures above. Which of these two contains a stereocenter? Draw thestructure on your answer sheet and mark the stereocenter with an asterisk. 82. Which of these two is a chiral molecule? Explain your answer. 83. Which of these two can exist as a pair of enantiomers? 84. Draw the pair of enantiomers using three-dimensional representation.arrow_forward
- Consider molecules with more than one chiral center. Consider 2,3-dyhdroxybutanoic acid. a. How many chiral centers does it have? b. Which ones? c. Reproduce the structure and encircle the four groups, which are linked to each chiral carbon.arrow_forwardDetermine the number of possible stereoisomers that exist for the compound C(CH2CHOHCH3)4. Compute the maximum number that you would predict using the 2n rule. Using the notation RRRR, list all of the stereoisomers and identify all pairs of enantiomers and diastereomers. Do any meso structures exist? Note, the notation RRRR indicates that all four stereocenters in the molecule have the R configuration.arrow_forwardDraw the cis isomer of the structure shown below. D • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • In cases where there is more than one answer, just draw one. If the structure does not have cis/trans isomers, simply redraw the molecule without stereobonds.arrow_forward
- 3. Draw the structural formula of 3-bromo-2-chloropentane. Identify the chiral carbons with asterisks. Using 2n formula (n is number of chiral centers) calculate the number of stereoisomers. Construct 2 pairs of mirror images. Take one pair of the enantiomers, compare it with the either of the models of the second pair of enantiomers. Are these two molecules mirror images? Draw the fisher projections of the four stereoisomers and identify diastereomers.arrow_forwardStereoisomers are isomers that differ in spatial arrangement of atoms, rather than connectivity of atoms. Stereoisomers have different properties, especially in biological systems. Which is the stereochemical relationship between this pair of molecules? OH "OH 8p OH OH ...||| 4 A) enantiomers B) diastereomers C) identical compounds D) constitutional isomers E) Not isomersarrow_forwardDraw the structure(s) of all of the possible monochloro derivatives of 2,2-dimethylpropane, C3H11CI. • You do not have to consider stereochemistry. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right co Separate structures with + signs from the drop-down menu. opy aste ChemDoodle >arrow_forward
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