Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 1, Problem 1.49SP
If the carbon atom in CH2Cl2 were fat. there would be two stereoisomers The carbon atom in CH2Cl2 is actually tetrahedral. Make a model of this compound, and determine whether there are any stereoisomers of CH2Cl2.
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Build 2‑bromoethan‑1‑ol and its mirror image.
2‑Bromoethan‑1‑ol, which has condensed structural formula BrCH2CH2OH, is also called 2‑bromoethanol.
a. Draw the structures of 2‑bromoethan‑1‑ol and its mirror image using wedges and dashed wedges.
b. How many stereocentres are present in 2‑bromoethan‑1‑ol?
c. Are the molecules chiral? Do they contain planes of symmetry? Briefly explain the evidence for your answer.
Build 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.
Can cis-1,2-dibromocyclopentane exist as a pair of enantiomers? Draw all structures and make appropriate models to check it out. Try the same thing (structures and models) for trans-1,2-dibromocyclopentane. Draw both. Are these enantiomers? Show R and S for all asymmetric centers.
Chapter 1 Solutions
Organic Chemistry (9th Edition)
Ch. 1.2C - a. Nitrogen has relatively stable isotopes...Ch. 1.4 - Draw Lewis structures for the following compounds....Ch. 1.5 - Write Lewis structures for the following molecular...Ch. 1.5 - Circle any lone pairs (pairs of nonbonding...Ch. 1.6 - Use electronegativities to predict the direction...Ch. 1.8 - Prob. 1.6PCh. 1.9B - Draw the important resonance forms for the...Ch. 1.9B - Prob. 1.8PCh. 1.9B - Prob. 1.9PCh. 1.9B - Use resonance structures to identify the areas of...
Ch. 1.10A - Draw complete Lewis structures for the following...Ch. 1.10B - Give Lewis structures corresponding to the...Ch. 1.10B - Prob. 1.13PCh. 1.11 - Compute the empirical and molecular formulas for...Ch. 1.16 - a. Use your molecular models to make ethane, and...Ch. 1.17 - a. Predict the hybridization of the oxygen atom in...Ch. 1.17 - Predict the hybridization geometry and bond angles...Ch. 1.17 - Predict the hybridization, geometry, and bond...Ch. 1.17 - Prob. 1.19PCh. 1.17 - Allene, CH2=C=CH2, has the structure shown below...Ch. 1.17 - 1. Draw the important resonance forms for each...Ch. 1.18B - Prob. 1.22PCh. 1.18B - Two compounds with the formula CH3CH=NCH3 are...Ch. 1.19B - Prob. 1.24PCh. 1.19B - Give the relationship between the following pairs...Ch. 1 - a. Draw the resonance forms for SO2 (bonded OSO)....Ch. 1 - Name the element that corresponds to each...Ch. 1 - Prob. 1.28SPCh. 1 - For each compound, state whether its bonding is...Ch. 1 - a. Both PCl3 and PCl5 are stable compounds Draw...Ch. 1 - Draw a Lewis structure for each species a. N2H4 b....Ch. 1 - Prob. 1.32SPCh. 1 - Prob. 1.33SPCh. 1 - Draw Lewis structures for a. two compounds of...Ch. 1 - Prob. 1.35SPCh. 1 - Some of the following molecular formulas...Ch. 1 - Prob. 1.37SPCh. 1 - Give the molecular formula of each compound shown...Ch. 1 - 1. From what you remember of electronegativities,...Ch. 1 - For each of the following structures, 1. Draw a...Ch. 1 - Prob. 1.41SPCh. 1 - Prob. 1.42SPCh. 1 - Prob. 1.43SPCh. 1 - Prob. 1.44SPCh. 1 - For each pair of ions, determine which on is more...Ch. 1 - Use resonance structures to identify the areas of...Ch. 1 - Prob. 1.47SPCh. 1 - In 1934, Edward A. Doisy of Washington University...Ch. 1 - If the carbon atom in CH2Cl2 were fat. there would...Ch. 1 - Cyclopropane (C3H6, a three-membered ring) is more...Ch. 1 - Prob. 1.51SPCh. 1 - Prob. 1.52SPCh. 1 - In most amines, the nitrogen atom is sp3...Ch. 1 - Predict the hybridization and geometry of the...Ch. 1 - Draw orbital pictures of the pi bonding in the...Ch. 1 - Prob. 1.56SPCh. 1 - Prob. 1.57SPCh. 1 - Which of the following compounds show cis-trans...Ch. 1 - Give the relationships between the following pairs...Ch. 1 - Dimethyl sulfoxide (DMSO) has been used as an...
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- Using your model, construct an energy diagram to show the variation in the free energy of the molecule as the FRONT ATOM is rotated CLOCKWISE from 0º to 360º in 60º increments. In your energy diagram, you should clearly show the relative energies of each conformer.arrow_forwardWhat is the maximum number of stereoisomers that can exist for this molecule? Can you help me, please? can you explain to me please?arrow_forwardThere are several different types of isomers. Below are four molecules that all have the same molecular formula, but are not identical. Name the molecules. Do not forget the configuration of the stereocentres.b.Which pairs of molecules are constitutive isomers, enantiomers, diastereomers, or identical? (Note there are six pairs: 1-2, 1-3 1-4, 2-3, 2-4, and 3-4)arrow_forward
- Stereoisomers share the same connectivity and differ only in the way their atoms are arranged in space. Draw the structure of a compound that is a stereoisomer of cis-1,4-dibromocyclohexane.(Note that the question asks for a different stereoisomer of the named compound and not the named compound itself.)Use the wedge/hash bond tools to indicate stereochemistry where it exists.In cases where there is more than one answer, just draw one.arrow_forwardCannot be hand-drawn - type or computer illustrate Help correct my work - Calculate the maximum number of possible stereoisomers of your molecule using the following formula: ▪ Maximum number of possible stereoisomers = 2n (where n= the number of chiral carbons in your molecule). This calculation does not include E- or Z- isomers for any compounds containing double bonds o illustrate the possible stereoisomers of the molecule.arrow_forwardConsider 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_forward
- How many asymmetric/chiral centers are present in the molecule below?arrow_forwardMolecules that have the same molecular formula, but different atomic connections are called constitutional isomers. Draw and name the five constitutional isomers of C6H14. Is this correct answer from this paper that I draw for the name the five constitutional isomers of C6H14? Can you explain to me that why is the different atomic connections are called constitutional isomers?arrow_forwardIdentify and label all functional groups Identify and label all stereo centersarrow_forward
- (a) Draw the nine isomers having the formula C7H16 . (Hint: There is one structure with a seven-carbon chain, two structures with six-carbon chains [one is illustrated in the margin above], five structures with a five-carbon chain, and one structure with a fourcarbon chain.)(b) Identify the isomers of C7H16 that are chiral.arrow_forwardConstruct the three-dimensional model of 2-methylhexane, also draw the anti and gauche models where the rotation between carbons 3 and 4 is clearly appreciated.arrow_forwardCompounds with several chiral centres may have configurations referred to as meso. Meso configurations arise when the molecule can adopt a configuration with an internal mirror plane. When this occurs, the mirror image of a molecule with an internal mirror plane is an identical configuration. Thus, even though the molecule may possess several chiral centres, they are reflection of each other (within the molecule) thus resulting in an achiral meso form. This occurs for example for tartaric acid (Figure 3.1). Because of this, tartaric acid only has three stereoisomers instead of four. It has the two chiral (R,R) and (S,S) enantiomers, and the meso form. Figure 3.1. Stereoisomers of tartaric acid. Given the information above on meso forms, how many different stereoisomers do compounds A to D (Figure 3.2) have? Figure 3.2. Structure of compounds A, B, C and D.arrow_forward
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