Concept explainers
Interpretation:
When cyclohexane is substituted by an ethynyl group, the energy difference between axial and equatorial conformations is only
Concept Introduction:
The difference in strain energy between the axial and equatorial conformations can be calculated by the ratio at equilibrium using the equation of the Gibb’s free energy (
The terms in the above equation are explained as
The universal gas constant value is
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Chapter 2 Solutions
Organic Chemistry
- Compounds 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_forwarddraw structural formulas for all isomeric alkanes with molecular formula C7H16. Predict which isomer has the lowest boiling point and which has the highest boiling point.arrow_forwardThe sex attractant of the female tiger moth is an alkane of molecular formula C 18H 38. Is this molecule an acyclic alkane or a cycloalkane?arrow_forward
- Compounds X and Y have the formula C6H12- Both X and Y react with one molar equivalent of hydrogen in the presence of a palladium catalyst to form 2-methylpentane. The heat of hydrogenation of X is less than that of Y. X and Y react with HBr to form a mixture of the same bromoalkanes, and they both undergo hydroboration/oxidation to give a mixture of the same alcohols. What is the structure of Y? In cases where there is more than one answer, just draw one. n. n [ ]# ChemDoodleⓇ zaarrow_forwardDifferentiate Cyclohexane vs Benzenearrow_forwardPyrethrins, such as jasmolin II (shown below), are a group of natural compounds that are synthesized by flowers of the genus Chrysanthemum (known as pyrethrum flowers) to act as insecticides. CH3 CH2=CH-CH. CH-C- -HCS 0-CH, CH,-C H2C- ČH, Which is not a functional group or structural feature in jasmolin II? cycloalkane carboxylic acid ester alkenearrow_forward
- Draw a structural formula for cis-1-bromo-3-chlorocyclohexane.arrow_forwardGlucose, C6H12O6, contains an aldehyde group but exist predominantly in the form of the cyclic hemiacetal show below. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. Identify which carbon provides the —OH group and which provides the —CHO? Give a functional isomer of glucose and draw its structure.arrow_forwardCompounds 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_forward
- Alkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a β-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH4 reduces the C–Hg bond to a C–H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structures of the Hg-containing compound(s) and the final alcohol product(s) formed in the following reaction sequence, omitting byproducts. If applicable, draw hydrogen at a chirality center and indicate stereochemistry via wedge-and-dash bonds.arrow_forwardWhat is the structure of a compound with the formula C7H14O that has an ether and cyclobutane ring, including its IUPAC name? In addition, what is the structure of the compound with the formula C7H14O that does NOT contain the functional groups: epoxide, ether, cycloalkane, alcohol, alkene. Indicate the functional groups used that are present in the structure made for this compound.arrow_forward
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