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29 Cards in this Set

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  • Back
Cycloalkanes have what general formula if they have one ring?
CnH2n
# C atoms in ring > # C atoms in largest substituent
alkyl substituted cycloalkane
# C atoms in largest substituent > # C atoms in the ring
cycloalkyl substituted alkane
Numbering Cycloalkanes
start at a point of attachment and number so that the second substituent has the lowest possible number
Cycloalkanes have ______ rotational freedom than alkanes
less
2 substituents on the same face
cis disubstituted
2 substituents on opposing faces
trans disubstituted
2 stereoisomers will be connected in the _____ order but in ______ spatial orientation.
same, different
Cis-trans isomers are _______ that ______ be interconverted
stable compounds, cannot
The more strained a compound the _______ the heat of combustion
higher
Angle Strain
occurs when bond angles are distorted from their normal values (leads to instability)
Torsional Strain
is due to eclipsing of bonds
Steric Strain
results when atoms approach too closely (repulsive interactions)
Cyclopropane has _____ strain and ______ strain
angle strain, torsional strain
Cyclopropane is drawn as?
planar triangle
Weak bonds are more or less reactive?
more reactive
Cyclobutane has ______ angle strain than cyclopropane but more ______ strain
angle, torsional
Cyclobutane is drawn as?
a square with C slightly bent out of plane to relieve strain
Cyclopentane has ______ angle strain but considerable ______ strain
little, torsional
Cyclopentane is drawn as?
an enveloped pentagon with C-5 bent out of plane and H nearly staggered
The chair conformation of cyclohexane is?
strain free
The twist boat conformation of cyclohexane has little ______ strain but experiences both _____ and _____ strain,
angle, steric, torsional
Axial hydrogens lie?
perpendicular to the plane of the ring
Equatorial hydrogens lie?
roughly in the plane of the ring
Each carbon has _____ axial and _____ equatorial hydrogen
one, one
After a ring flip ______ bonds become _______ bonds
axial, equatorial
Monosubstituted cyclohexane is most stable when substituents are in the ______ position
equatorial
Axial methylcyclohexane is less stable than equatorial due to?
1,3 diaxial interactions
The amount of strain induced by a 1,3 diaxial interaction depends on?
the size of the groups involved