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Organic Chemistry Week 6 Notes

by: Raghad Kodvawala

Organic Chemistry Week 6 Notes 2510

Marketplace > Ohio State University > 2510 > Organic Chemistry Week 6 Notes
Raghad Kodvawala
Organic Chemistry 1
Dr. Cunningham

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Week 6 Notes
Organic Chemistry 1
Dr. Cunningham
Class Notes
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This 3 page Class Notes was uploaded by Raghad Kodvawala on Monday March 14, 2016. The Class Notes belongs to 2510 at Ohio State University taught by Dr. Cunningham in Spring 2016. Since its upload, it has received 10 views.


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Date Created: 03/14/16
Chapter 4 Cycloalkanes 41 Names and Ph sical Pro erties of C cloalkanes The names of cycloalkanes follow IUPAC rules 0 Alkane names are preceded by the pre x cyclo Disubstituted cycloalkanes can be stereoisomers o Cis when substituents are on the same face 0 Trans when substituents are on opposite faces 0 Stereoisomers compounds that have identical connectivities but differ in the arrangement of their atoms in space 0 The properties of the cycloalkanes differ from those of their straightchain analogs o Cycloalkanes have higher boiling and melting points as well as higher dens es Due to increased London interactions of the relatively rigid and symmetric cycloalkanes W 0 Ring strain when the bond angles in a cycloalkane differ signi cantly from the bond angles in a branched alkane The heats of combustion of the cycloalkanes reveal the presence of ring strain 0 Small rings cyclopropane cyclobutane 0 Common rings cyclopentane cyclohexane cycloheptane 0 Medium rings 812 membered rings 0 Large rings 13membered and larger 0 Strain affects the structures and conformational function of the smaller cycloalkanes o Cyclopropane is very unstable for such a small molecule ln cyclopropane all of the alkane groups are eclipsing one another lt39s C C C bond angles are 60 which is a signi cant deviation from the normal 1095 in tetrahedral carbon Bond angle strain the energy needed to distort the tetrahedral carbons enough to close the ring 0 Cyclobutane Not planar but quotpuckeredquot in a 3D shape Not rigid continually rapidly quot ippingquot between quotpuckeredquot con gurations K o Cyclopentane gc7 Qf S quotEnvelopesquot quotHMhairsquot Chapter 4 Cycloalkanes 43 C clohexane A StrainFree C cloalkane The chair conformation of cyclohexane is strain free FN M39squot Cyclohexane also has several less stable conformations Cyclohexane has axial and equatorial hydrogens 0 Axial groups nearly parallel to the molecular axis 0 Equatorial groups nearly perpendicular to the principal molecular axis closer to the equatorial plane 0 How to Draw Chair Cyclohexanes 0 Draw the chair and arbitrarily number the carbons parallel parallel 0 Add all the axial bonds as vertical lines pointing downward C1 C3 C5 and upward at C2 C4 C6 l l 4 lg l1 3 0 Draw the two equatorial bonds at C1 and C4 parallel to the bond between C2 and C3 Conformational ipping interconverts axial and equatorial hydrogens 44 Substituted C clohexanes Axial and equatorial methylcyclohexanes are not equivalent in energy Chapter 4 Cycloalkanes o In the equatorial conformer the methyl group extends into space away from the rest of the molecule 0 In the axial conformer the methyl substituent is close to the other two hydrogens Substituents compete for equatorial positions 0 To predict the more stable conformer of a more highly substituted cyclohexane the cumulative effect of placing substituted cyclohexane the cumulative effect of placing substituents either axially or equatorially must be considered WW Cycloalkanes larger than cyclohexane have more strain 0 The molecule equilibrates among several geometries that are very close in energy 0 Strainfree conformations are attainable only for large cycloalkanes The carbon chain adopts a structure very similar to that of straightchain alkanes WWW Polycyclic alkanes may contain fused or ridged rings 0 Fused when two cycloalkanes share two adjacent carbon atoms 0 Fused bicyclic compounds constructed from two rings fused together 0 Ringfusion carbons the shared carbons o Ringfusion substituents groups attached to ringfusion carbons


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