Organic Chemistry Chapter 4 Essay

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alkanes and cycloalkanes are hydrocarbons in which all the
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carbon-carbon bonds are single bonds
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hydrocarbons that contain carbon double bonded to carbon is an
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alkene
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hydrocarbons that contain carbon triple bonded to carbon is an
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alkyne
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formula for alkanes is
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CnH2n+2
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formula for cycloalkanes is
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CnH2n
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what type of hybridization and shape do alkanes and cycloalkanes have
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sp3 tetrahedral
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even “straight chain” alkanes are not straight they have a
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zigzag geometry
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examples of straight chain unbranched alkanes are
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butane and pentane
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examples of branched chain alkanes are
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isobutane and neopentane
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butane and isobutane have same molecular formula (C4H10) but have different bond connectivities so they are
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constitutional isomers
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the # of constitutional isomers increases rapidly with
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the number of carbons
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constitutional isomers usually have different
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physical properties
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why do constitutional isomers have diff physcial props
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as we change change we change intermolecular forces which changes properties diff SA=diff intermolec forces
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most commonly used nomenclature system is the
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IUPAC system
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what is the common name for 2-propanol
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isopropanol
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1st rule of naming branched-chain alkanes is
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use longest continuous carbon as parent name
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2nd rule of naming branched-chain alkanes is
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use the lowest number of the sustitiuent
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3rd rule of naming branched-chain alkanes is
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use number obtained by rule 2 to designate location of substituent
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4th rule of naming branched-chain alkanes is
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for 2 or more sub use lowest individual number of parent chain, sub listed in alphabetical order disregarding multiplying prefixes such as di and tri
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5th rule of naming branched-chain alkanes is
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when 2 sub identical on same carbon use that number twice
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6th rule of naming branched-chain alkanes is
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for identical sub use prefixes such as di, tri, tetra, ect
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7th rule of naming branched-chain alkanes is
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2 chains with equal length compete for parents chain choose one with greater number of subs
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8th rule of naming branched-chain alkanes is
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when branching first occurs at equal distance from either end of longest chain, choose name that gives lower number at the first point of difference
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we classify hydrogen atoms by
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what they are connected too
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halogens are treated as
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substituents with prefix such as fluor, chloro, bromo, iodo
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naming alcohols you select longest continuous chain to which the what is directly attached? how do you change name of alkane
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hydroxyl change -e to -ol
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number longest carbon chain that gives carbon bearing the OH the what? indicate what of OH?
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lower number position
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what prefix do you attach to cycloalkanes with only one ring
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cyclo-
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when more then one ring system is attached to a single chain you name it is
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dicyclo
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bicycloalkanes are alkanes containing
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two fused or bridged rings
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when naming alkenes begin numbering at the end of chain closest to
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carbon carbon double bond
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naming alkenes assign location of carbon double bond by
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using number of first atom of carbon double bond as the prefix
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naming alkenes indicate locations of the substitiuent groups by the numbers of the
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carbon atoms to which they are attached
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naming alkenes number substituted cycloalkenes in way that gives carbon atoms of double bond the (2 things)
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1 and 2 position and sub groups lower numbers at first point of difference
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name compounds containing double bond and alcohol group as alkenols and give alcohol carbon the
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lower number
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two identical or sub groups on same side of carbon double bond is
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cis
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two identical or sub groups on opposite sides of carbon double bond i
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trans
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alkynes named in same way as alkenes except
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ending name is changed to -yne
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OH group has priority over
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carbon triple bond
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two groups bonded by a single bond can undergo (with respect to each other)
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rotation about that bond
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temporary molecular shapes that result from a rotation about a single bond
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conformations
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each possible structure of conformation
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conformer
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analysis of energy changes that occur as a molecule undergoes rotations about single bond
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conformational analysis
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cycloalkanes do not have the same relative stability due to
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ring strain
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ring strain comprises
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angular and torsional strain
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result of deviation from idea bond angles caused by inherent structural constraints
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angular strain
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result of dispersion forces that cannot be relieved due to restricted conformational stability
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torsional strain
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cyclobutane ring is not planar but is actually slightly
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folded
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what type of conformation does cyclopentane have
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slightly bent
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what are the two conformers of cyclohexane
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chair and boat form
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what conformation of cyclohexane is less stable and why
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boat higher energy
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what conformation has lower energy than pure boat form conformation and how stable is this conformation compared to the chair form
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twist boat and not as stable as chair form
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what ring is most commonly found in nature
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6 membered ring
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the chair conformation of cyclohexane has two distinct orientations for the bonds that project from the ring which are termed as
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axial and equatorial
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axial hydrogen atoms are either
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up or down in a vertical column
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equatorial hydrogen atoms are
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all angled slightly
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when drawing chair conformational structures try to make corresponding bonds
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parallel in your drawing
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for methylcyclohexane the chair conformation with axial G is less stable due to
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1,3-diaxial interaction
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the larger the G group the more severe the (2 parts)
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1,3-diaxial interaction and shifted of equilibrium from axial G form chair to equatorial
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the chair conformation with what group is less stable due to 1,3-diaxial interaction
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axial tert-butyl group
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upper lower bonds means the groups are
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trans
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alkanes, as a class, are characterized by general
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inertness to many chemical reagents
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C-C and C-H bonds are quite (how do they break?)
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strong only break when alkanes heated to very high temps
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because C and H atoms have nearly same EN the C-H bonds of alkanes are only
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slightly polarized
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this low reactivity of alkanes toward reagents accounts for the fact that alkanes were originally called what? what does this name mean
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paraffins little affinity
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the difference in the number of pairs of hydrogen atoms between the compound under study and an acyclic alkane having the same number of carbons
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index of hydrogen deficiency
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each double bond or ring for saturated acyclic alkanes
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has 2 hydrogens less
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each double bond or ring provides
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one unit of hydrogen deficiency
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when calculating IHD for compounds containing halogens count atoms as though they are
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hydrogen atoms
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when calculating IHD for compounds containing oxygen
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ignore oxygen atoms and calc IHD from remainder of formula
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when calculating IHD for compounds containing nitrogen
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subtract one hydrogen from each nitrogen atom and ignore nitrogen atoms
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nature perfers states of
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lower PE
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steric factors (spatial factors) can affect the
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stability and reactivity of molecules
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like charges
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repel

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