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Chapter 3 part 2 student notes

Uploaded by

gdaaku09
Copyright
© © All Rights Reserved
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Cycloalkanes

• Alkanes that contain rings of carbon atoms


• Whether or not a cycloalkane exists or not depends
on the
• General formula is

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• Like the acyclic alkanes, they are non-polar compounds with low
reactivity
• Capable of , their mp and bp are influenced only by
their molecular weight and shape.
• They are dense than water.

2
Cycloalkane Nomenclature
• Cycloalkane is the main chain: alkyl groups attached to the
cycloalkane will be named as alkyl groups.
• If only one alkyl group is present, then no numbers are
required.
• If there are , number the main chain
to give all substituents the lowest possible number.
H3C CH3
CH3

CH2CH3
CH3

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If the acyclic portion is a larger percentage of the molecule
or if it contains a higher priority functional group, name the
cyclic portion as a
Cis/Trans (Geometric) Isomers
• Similar to alkenes, cycloalkanes can have
• Cis: both substituents on the side of the ring
• Trans: substituents on sides of the ring
• This is indicated in the name by writing cis or trans at the front of the
name.

CH3 H H H

H CH3 H3C CH3

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Ring Strain of Cycloalkanes
• rings are the most common in nature.
• Carbons of cycloalkanes are sp3 hybridized and thus require an angle
of 109.5.
• When a cycloalkane has an angle other than 109.5, there will not be
and the compound will have
• Angle strain is sometimes called Baeyer strain in honor of Adolf von
Baeyer who first explained this phenomenon.

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8
• Torsional strain arises when all the bonds are eclipsed.

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Figure 3-14

10
• Cyclopentane
-has bond angles of , so its close to ideal, but the hydrogens are in
the conformation
-to reduce the eclipsing, the molecule

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Cyclohexane Conformations
• Cyclohexane achieves tetrahedral bond angles &
conformations by

Figure 3-19

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Figure 3-20
13
• conformation is most stable & usually
preferred
• Due to less interactions compared to

Figure 3-21
14
• Draw the chair conformer:

• Draw the ‘flipped’ chair conformer:

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around the carbon
atoms in
cyclohexane.

Figure 3-22
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Conformation of Monosubstituted
Cyclohexanes
• The favored
conformation of
mono-sub
cyclohexanes is
normally the one
with the substituent
at the
• Due to steric factors
in the
Figure 3-23

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• These unfavorable steric interactions when a group is axial are called

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• This means it is better to have a substituent in an
equatorial conformation than in a axial conformation

Figures 3-
24 & 3-25

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• Draw the most stable conformation of ethylcyclohexane.

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Conformations of disubstituted
cyclohexanes
• With 2 substituents present, the molecule can be either cis or trans
• Ex. 1,4-dimethylcyclohexane

Positions Cis Trans


1,2
1,3
1,4

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• With 2 substituents, it is recommended to write both
possible conformers with a
• This is done to test out where or if there are steric
interactions in the conformation.
• From this, we can determine if one conformer is
preferred.

Cis-1,3-dimethylcyclohexane 22
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• If 2 substituents are not equal in size it is more
favorable for the larger substituent to be in the
position

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