CYCLOBUTANE

a) Identification of the substance, its chemical name, its state under normal conditions
● C4H8 - Cyclobutane
● Cyclobutane are gases at room temperature
● Gas that condenses to a liquid at 55°F.
● cyclobutane is unstable above about 500 °C
● Insoluble in water.
● Have densities lower than that of water
● Soluble in alcohol, acetone and ether.
● colourless gas and commercially available as a liquefied gas
● Cyclobutane itself is of no commercial or biological significance, but more complex derivatives are
important in biology and biotechnology
b) Write the molecular formula, the graphical formula and the structural formula of the hydrocarbon
Molecular formula
C4H8 or CH3CH2CH=CH2
Graphical formula / Structural formula

c) Determine the classification of hydrocarbon (alkane, alkene, alkyne), its 3-dimensional structure
Cycloalkane
● is a saturated hydrocarbon in which carbon atoms are connected to one
another in a cyclic (ring) arrangement is present.
● The boiling points of continuous-chain cycloalkanes increase with an increase in carbon-chain length or
ring size
● Cycloalkanes have higher boiling points than their noncyclic counterparts
with the same number of carbon atoms
● For a series of cycloalkanes, melting point increases as carbon-chain length increases.
● Cycloalkanes are flammable
● Cycloalkanes are saturated hydrocarbons in which at least one cyclic arrangement of carbon atoms is
present.
 ● The formulas of all cycloalkanes can be represented by the general formula CnH2n, where n is the
number of carbon atoms present
● Cycloalkanes lack functional groups; as a result, they are relatively unreactive.

Its 3d structure is not planar, but rather a bent/twisted ring (puckered, in which hydrogen atoms are
twisted away from each other)

● The four carbon atoms in cyclobutane are not coplanar; instead the ring typically adopts a folded
conformation.
● One of the carbon atoms makes a 25° angle with the plane formed by the other three carbons. In this
way some of the eclipsing interactions are reduced.

d) Determine the type of hybridization

Cyclobutane generally features an sp3 hybridization, since the bonds formed between the carbon atoms
are single bonds.

e) Determine the types of bonds present, bond length between C-H and C-C and, the bond angle.
 ● Cyclobutane is forced to form bond angles much smaller than the preferred 109.5° bond angles.
Cyclobutane can easily react in order to obtain the preferred 109.5° bond angles
● Cyclobutane looks like it should have an angle of 90° (like a square), but it actually has an angle of 88°,
which is far from the ideal angle of 109.5°. Cyclobutane adopts a nonplanar “puckered” conformation
(bond angle of 88°) to reduce the torsional strain that is a characteristic of planar conformation (bond
angle of 90°).
● Planar cyclobutane would have even greater torsional strain that cyclopropane because of the greater
number of eclipsing interactions
● Cyclobutane can pucker to partially alleviate torsional strain, but bond angle strain is still significant.
● The structure of cyclobutane reveals that this molecule is not planar but puckered, with an approximate
bending angle of 26°. The non planar structure of the ring, however, is not very rigid. The molecule
"flips'' rapidly from one puckered conformation to the other. Puckered cyclobutane is a highly dynamic
(fluxional) molecule, with a barrier between puckered forms of about 1.5 kcal/mol. Distorting the four-
membered ring from planarity is favorable: It partly relieves the strain introduced by the eight eclipsing
hydrogens.

C-H bonds (8)

C-C bonds (4)
BOND LENGTHS
The angstrom or ångstrom (Å) is an internationally recognized unit of length equal to 1 × 10-10 meters (m) or 0.1 nanometer (nm).

ATOM 1 ATOM 2 LENGTH

C1 C3 1.555 Å

C1 C4 1.555 Å

C1 H5 1.093 Å

C1 H6 1.091 Å

C2 C3 1.555 Å

C2 C4 1.555 Å

C2 H7 1.093 Å

C2 H8 1.091 Å

C3 H9 1.093 Å

C3 H10 1.091 Å

C4 H11 1.093 Å

C4 H12 1.091 Å

ANGLES
Cyclobutane is a non-planar, bent molecule. By deviating from planarity, the eight hydrogen atoms are eclipsed
resulting in decreased strain. Part of the molecule is rotated out of the plane by 26°. However, this does not
imply that the structure is rigid; it interconverts rapidly from one bent conformation to another. The C-C-C
angle of 88.5° still is clearly different from a tetrahedral angle (109.5°) indicating high ring strain.