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Chapter 4
Cycloalkanes
18
Organic Chemistry
Undergraduate 2
09/22/2014

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Term
cyclo-
Definition
the prefix used to denote alkanes with the empirical formula CnH2n
Term
cycloalkyl radicals
Definition
radicals derived from cycloalkanes by abstraction of a hydrogen atom
Term
cis
Definition
substituents on a cycloalkane located on the same face
Term
trans
Definition
substituents on a cycloalkane located on opposite faces
Term
stereoisomers
Definition
compounds that have identical connectivities but differ in their arrangement of their atoms in space
Term
cis and trans isomers can be interconverted only by _____ bonds
Definition
breaking
Term
conformers are readily equilibrated by _____ about bonds
Definition
rotation
Term
4 groups of cycloalkanes
Definition
1. small rings (cyclopropane, cyclobutane)
2. common rings (cyclopentane, cyclohexane, cycloheptane)
3. medium rings (from 8- to 12- membered)
4. large rings (13-membered & larger)
Term
chair conformation of cyclohexane
Definition
carbons 1 & 4 are moved out of planarity in opposite directions; resembles a chair; eclipsing is completely absent; bond angles are nearly tetrahedral
Term
boat form of cyclohexane
Definition
a less stable conformation of cyclohexane; carbons 1 & 4 are out of plane in the same direction
Term
transannular strain
Definition
strain resulting from steric crowding of two groups across a ring
Term
is boat form or twist-boat/skew-boat conformation of cyclohexane more stable?
Definition
twist-boat/skew-boat conformation
Term
axial
Definition
carbon-hydrogen bonds that are nearly parallel to the principle molecular axis
Term
equatorial
Definition
carbon-hydrogen bonds that are nearly perpendicular to the axis & close to the equatorial plane
Term
1,3-diaxial interaction
Definition
when transannular strain is due to axial substituents on carbon atoms that have a 1,3-relation
Term
the axial substituent is _____ to two of the ring carbons (C3 and C3')
Definition
gauche
Term
when the substituent is in the equatorial position, it is _____ to two of the ring carbons (C3 and C3')
Definition
anti
Term
two forms of chair methylcyclohexane are in equilibrium; which conformer is more stable?
Definition
equatorial
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