The Chemistry of the Cyclopropyl Group

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Cyclopropane is significantly more reactive than what is expected because of the bond angles in the ring.

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Normally, when carbon forms four single bonds, the bond angles are approximately With the electron pairs this close together, there is a significant amount of repulsion between the bonding pairs joining the carbon atoms, making the bonds easier to break. The carbon atom with the alcohol substituent must be labeled as 1. Molecules containing an alcohol group have an ending " -ol ", indicating the presence of an alcohol group.

If there are two alcohol groups, the molecule will have a "di-" prefix before "-ol" diol. If there are three alcohol groups, the molecule will have a "tri-" prefix before "-ol" triol , etc. The alcohol substituent is given the lowest number even though the two methyl groups are on the same carbon atom and labeling 1 on that carbon atom would give the lowest possible numbers. Numbering the location of the alcohol substituent is unnecessary because the ending "-ol" indicates the presence of one alcohol group on carbon atom number 1.

There are many other functional groups like alcohol, which are later covered in an organic chemistry course, and they determine the ending name of a molecule. The naming of these functional groups will be explained in depth later as their chemical properties are explained.

Aromatic, Antiaromatic, or Nonaromatic, Huckel's Rule, 4n+2, Heterocycles, Aromaticity

Although alkynes determine the name ending of a molecule, alkyne as a substituent on a cycloalkane is not possible because alkynes are planar and would require that the carbon that is part of the ring form 5 bonds, giving the carbon atom a negative charge. However, a cycloalkane with a triple bond-containing substituent is possible if the triple bond is not directly attached to the ring.

Name the following structures. Note: The structures are complex for practice purposes and may not be found in nature. Name the following compounds:. Draw the following structures. Steven Farmer Sonoma State University. Study Notes Provided that you have mastered the IUPAC system for naming alkanes, you should find that the nomenclature of cycloalkanes does not present any particular difficulties.

Introduction Many organic compounds found in nature or created in a laboratory contain rings of carbon atoms with distinguishing chemical properties; these compounds are known as cycloalkanes. Cyclohexane, for example, has a ring structure that looks like this: Figure 4. In this arrangement, both of these atoms are either pointing up or down at the same time In addition to being saturated cyclic hydrocarbons, cycloalkanes may have multiple substituents or functional groups that further determine their unique chemical properties.

Synthesis of cyclopropanes

Glucose 6 carbon sugar Ribose 5 carbon sugar Cholesterol polycyclic Although polycyclic compounds are important, they are highly complex and typically have common names accepted by IUPAC. Contents For simplicity, cycloalkane molecules can be drawn in the form of skeletal structures in which each intersection between two lines is assumed to have a carbon atom with its corresponding number of hydrogens. The parent chain is the one with the highest number of carbon atoms. If there are two cycloalkanes, use the cycloalkane with the higher number of carbons as the parent chain.

If there is an alkyl straight chain that has a greater number of carbons than the cycloalkane, then the alkyl chain must be used as the primary parent chain. Cycloalkane acting as a substituent to an alkyl chain has an ending "-yl" and, therefore, must be named as a cycloalkyl.

The Chemistry of the Cyclopropyl Group, Volume 2

Cycloalkane Cycloalkyl cyclopropane cyclopropyl cyclobutane cyclobutyl cyclopentane cyclopentyl cyclohexane cyclohexyl cycloheptane cycloheptyl cyclooctane cyclooctyl cyclononane cyclononanyl cyclodecane cyclodecanyl Example 4. Example 4. Reactivity Cycloalkanes are very similar to the alkanes in reactivity, except for the very small ones, especially cyclopropane. Other Substituents on Cycloalkanes There are many other functional groups like alcohol, which are later covered in an organic chemistry course, and they determine the ending name of a molecule.

Name Name ending alkene -ene alkyne -yne alcohol -ol ether -ether nitrile -nitrile amine -amine aldehyde -al ketone -one carboxylic acid -oic acid ester -oate amide -amide Although alkynes determine the name ending of a molecule, alkyne as a substituent on a cycloalkane is not possible because alkynes are planar and would require that the carbon that is part of the ring form 5 bonds, giving the carbon atom a negative charge. Summary Determine the parent chain: the parent chain contains the most carbon atoms.


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Number the substituents of the chain so that the sum of the numbers is the lowest possible. Name the substituents and place them in alphabetical order. If stereochemistry of the compound is shown, indicate the orientation as part of the nomenclature. Cyclic hydrocarbons have the prefix "cyclo-" and have an "-alkane" ending unless there is an alcohol substituent present. When an alcohol substituent is present, the molecule has an "-ol" ending. Glossary alcohol : An oxygen and hydrogenOH hydroxyl group that is bonded to a substituted alkyl group.

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Cycloalkanes are alkanes with carbon atoms attached in the form of a closed ring. Problems Name the following structures. Answers to Practice Problems 1 cyclodecane 2 chlorocyclopentane or 1-chlorocyclopentane 3 transchloromethylcycloheptane 4 6-methylcyclopropyldecane 5 cyclopentylcyclodecane or 1-cyclopentylcyclodecane 6 1,3-dibromochlorofluorocycloheptane 7 1-cyclobutylisopropylcyclohexane 8 9 10 11 12 13 cyclohexane 14 cyclohexanol 15 chlorocyclohexane 16 cyclopentylcyclohexane 17 1-chloromethylcyclobutane 18 2,3-dimethylcyclopentanol 19 cismethylpropylcyclopentane.

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Please wait while we load your content Something went wrong. Try again? Cited by. Back to tab navigation Download options Please wait Article type: Communication. DOI: Download Citation: Chem. Rhodium-catalyzed tandem Pauson—Khand type reactions of 1,4-enynes tethered by a cyclopropyl group G. Chen and M. Shi, Chem.