Ch. 5 - ChiralitySee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins

We can use our knowledge of chiral centers to predict what types of stereoisomers molecules will make. 

Concept #1: Using chiral centers to predict types of stereoisomers. 

Concept #2: How to predict the total number of stereoisomers. 

Follow the 2n (n = stereocenters) rule to predict total number of possible stereoisomers.

Note: Remember that stereocenters include both chiral centers and trigonal centers!

Example #1: Draw all the stereoisomers for 2-bromocyclohexan-1-ol, and determine their relationships to each other.

Determine the total number of stereoisomers for the following molecule.

Example #2: Determine the total number of stereoisomers for the following molecule.

Additional Problems
Draw the enantiomer of the psychostimulant Focalin.
Determine if each statement is true or false. Write (T) or (F) on each line, respectively. a. A compound which has a non-superimposable mirror image is a chiral. b. Stereoisomers which are non-mirror images of each other are enantiomers c. A meso compound is achiral and therefore must never have stereocenters. d. Products produced from optically inactive starting materials will always be optically inactive.
There are  6 stereoisomers that have the name 2,5-dichloro-3-hexene. One of these stereoisomers is drawn in the box labeled “A”. Please note that this structure is drawn in a manner which shows the absolute stereochemistry clearly and unambiguously. In the box labeled “B”, draw the enantiomer of  A. In the box labeled “C”, draw the ACHIRAL diastereomer of A in which the double bond has the (Z) configuration. In the box labeled “D”, draw the  ACHIRAL diastereomer of A in which the double bond has the (E) configuration. Remember, a molecule is ACHIRAL when it IS superimposable on its mirror image! All of the structures that you draw should be line–angle structures! In each structure, use wedges, dashed wedges, and normal lines (as appropriate) to show the stereochemistry clearly and unambiguously.
Which of the following statements is (are) true about compounds a, b and c drawn below?   a. a and b are enantiomers of each other b. b and c are diastereomers of each other c. an equal mixture of a and b is optically active d. an equal mixture of a and c is optically active e. both b and c are true statements
   
Bromocyclobutane is an achiral molecule. Draw 4 chiral cyclic constitutional isomers of this molecule in the boxes provided. Make sure to place your answers in the correct boxes such that the sterochemical relationships between the molecules in your answers are as noted.
Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound? 
MARK WITH AN X EACH BOX THAT CORRESPONDS TO A CORRECT STATEMENT: (Notes: More than one box may be correct.) Diastereomers are enantiomers □, stereoisomers □ that are superimposable on their mirror image □, are not superimposable on their mirror image □, are not enantiomers □, and they are separable □, not separable □ from each other.
Draw all the stereoisomers for 1,2-cyclohexanediol and determine their relationships to each other
For the following compounda) Identify absolute configurations of all chirality centers.b) Draw its enantiomer
Draw all the stereoisomers of 1,2-diaminocyclohexane.(The amino substituent is -NH2, e.g. aminomethane would be CH3NH2.) Indicate which pairs of stereoisomers are enantiomers and which are diastereomers. Correctly identify the absolute configurations of any chiral centers.
Draw the enantiomer for each of the following compounds:
Draw the enantiomer for each of the following compounds:
Draw the enantiomer for each of the following compounds:
Draw the enantiomer for each of the following compounds:
(a) How many carbon atoms does an alkane (not a cycloalkane) need before it is capable of existing in enantiomeric forms?  
Draw the enantiomer for each of the following compounds:
Draw the enantiomer for each of the following compounds:
The structure of a chiral isomer is given below. Draw the mirror image isomer. Use wedge-and for the substituent groups, and be sure that the bonds convey tetrahedral geometry. 
What are enantiomers?1) nonsuperimposable mirror images2) superimposable mirror images3) molecules with different connectivity4) molecules with different molecular formulas