Answer 1:
Glucose occurs in both linear and cyclic
forms. In the linear form of the molecule,
five of the carbons (each single bonded to four
other atoms) are sp3 hybridized and one (the
carbon doubled bonded to oxygen and single bonded
to hydrogen) is sp2hybridized. Since the
hybridization of the orbitals determines the bond
angles, we know that the sp3 hybridized carbons
have bond angles of ~109.5 degrees (the ideal
angle for tetrahedral bonding) and sp2hybridized
carbons have bond angles of ~180 degrees. I have
attached astructure of glucose where I have
labeled the bond angles between someof the atoms
and also a 3D image of a linear glucose
molecule. glucose glucose-linear3DGlucose
can also occur in a pyranose form where it forms a
six membered ring, or in a furanose form where it
forms a five memberedring. When these rings are
formed, the reaction destroys the double bond in
the molecule so all of the atoms are sp3
hybridized. This means that they all want to have
bond angles of 109.5 degrees but the strain caused
by forming the ring prevents the angles from being
ideal.The pyranose form behaves much like
cyclohexane and exists in a"chair" conformation.
Due to the way the chair conformation is puckered,
it allows all of the atoms in the ring to assume
bond angles very close to 109.5 degrees. The
angles between the atoms in the ring will be ~
111.4 degrees and the angles between the atoms
attached to the ring will be ~107.6. I have
attached a 3D image of a pyranosering. glucose-pyranoseThe
furanose behaves similarly to cyclopentane. When
cyclopentanepuckers to achieve bond angles close
to 109.5 degrees, the hydrogens start bumping into
each other so to prevent this, the bond angles
have to be farther from ideal. Therefore this
conformation is more strained and less
energetically stable. The angles between atoms in
the ring will be ~104.4 degrees and the angles
between atoms attached to the ring will be ~106.0
degrees. References: Nelson, David L.,
and Michael M. Cox. "Chapter 7: Carbohydrates and
Glycobiology." Lehninger Principles of
Biochemistry. New York: W.H.Freeman, 2005. 241-44.
Print.
Vollhardt, K. Peter C., and Neil
Eric Schore. "Chapter 4: CyclicAlkanes." Organic
Chemistry: Structure and Function. New York:
W.H.Freeman and, 2003. 134-37. Print. Images
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