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Concept explainers
Interpretation:
The structural formulas for the cis and trans isomers of hydrindane has to be drawn in its most stable conformation and among the two drawn isomers, the more stable isomer has to be given.
Concept Introduction:
Cis, Trans Isomerism in Cycloalkanes:
When a cycloalkane ring has substituents on two or more carbon atoms, then the cycloalkane ring show a type of stereoisomerism called cis, trans isomerism.
Cis, trans isomers have same molecular formula and same connectivity of their atoms, but the arrangement of atoms in space would be different which be interconverted by rotation about single bonds.
In cis isomer, the substituents are on the same side of the ring.
In trans isomer, the substituents are on the opposite sides of the ring.
Bicycloalkane:
Bicycloalkanes are cycloalkane with two rings that are shared by two carbon atoms. The shared carbon atoms are called bridgehead carbons and the carbon chain connecting them is called a bridge.
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Chapter 2 Solutions
Organic Chemistry
- Only three stereoisomers are possible for 2,3-dibromo-2, 3-dichlorobutane. Draw them, indicating which pair are enantiomers (optical isomers). Why does the other isomer not have an enantiomer?arrow_forwardDraw the line bond structures for the following alkenes, cyclic alkenes, and alkynes: Can you explain to me about this part A) noncyclic alkenes that contain 4 carbon atoms (3 possible), please? Can you explain to me about this part B) cyclic alkenes that contain 4 carbon atoms (4 possible), please? Can you explain to me about this part C) alkynes that contain 4 carbon atoms (2 possible, neither of them is a cyclic alkyne), please?arrow_forwardWhich of the following statement is false about conjugated systems? A conjugated system is more stable than an unconjugated A system. The s-trans isomer is favored over the s-cis isomer. A conjugated system has C multiple resonance structures. A conjugated system can only D contain two alkenes.arrow_forward
- When cyclopropane is treated with HI, 1-idopropane is formed. A similar type of reaction does not occur with cyclopentene or Cyclohexane. Suggest an explanation for cyclopropane’s reactivity.arrow_forwardCompounds X and Y are stereoisomers having the formula C6H12.Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form hexane, and they each react with HBr to give a single bromoalkane product.Draw structural formulas for both X and Y.arrow_forward4. Which structure below represents the most stable conformation of cis-1-t-butyl-4-methylcyclohexane? A B D 5. The planar form of which ring would have bond angles close to the tetrahedral value, but is destabilized by eclipsing interactions (torsional strain)? Which of the following statements about conformations is FALSE? A) Conformations can be isolated and separated at room temperature B) Conformations are interconverted by rotation about o-bonds C) For butane the staggered anti conformation is the most stable D) For ethane the eclipsed conformation is the least stable 6. 7. Which of the following compounds has two chirality centers? .H H. H3Carrow_forward
- Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene C in an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forwardThere are 17 possible alkene isomers with the formula C6H12. Draw structures of the five isomers in which the longest chain has six carbon atoms, and give the name of each. Are any of these isomers chiral? (There are also eight isomers in which the longest chain has five carbon atoms, and four isomers in which the longest chain has four carbon atoms. How many can you find?)arrow_forwardFollowing are structural formulas for 1,4-dioxane and piperidine. 1,4-Dioxane is a widely used solvent for organic compounds. Piperidine is found in small amounts in black pepper (Piper nigrum). (a) Complete the Lewis structure of each compound by showing all unshared electron pairs. (b) Predict bond angles about each carbon, oxygen, and nitrogen atom. (c) Describe the most stable conformation of each ring and compare these conformations with the chair conformation of cyclohexane.arrow_forward
- Following is a structural formula for cortisol (hydrocortisone). Draw a stereo-representation of this molecule showing the conformations of the five- and six-membered rings.arrow_forward22. Which of the following statements is incorrect? Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the product in an endothermic reaction. Hammond-Leffler Postulate states that there is a strong resemblance between the transition state and the reactants in an exothermic reaction. The presence of more electron-donating alkyl groups ineffectively delocalize the positive charge in an organic molecule, making it less stable. The dehydration of primary alcohol proceeds via E2 mechanism. All of the abovearrow_forward∆H° values obtained for a series of similar reactions are one set of experimental data used to determine the relative stability of alkenes. Explain how the following data suggest that cis-but-2-ene is more stable than but-1-ene (Section 12.3A).arrow_forward
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