alkenes chp 13 Flashcards
what is the structure of an alkene
- contain at least 1 carbon-carbon double bond
what is the general fromula for aliphatic alkenes
aliphatic alkenes that contain 1 double bond have the general formula CnH2n
how many electrons does carbon have in its outer shell
each carbon atom has 4 electrons in its outer shell and can use these electrons to from bonds
which orbital is the electron that froms the pi bond in an alkene in
the P-orbital
How is a pi bond formed
a pi-bond is formed by the sideways overlap of 2 p-orbitals, in alkenes 1 from each carbon atom of the double bond
where is the electron density concentrated in a pi-bond
the pi electron density Is concentrated above and below the line joining the nuclei of the bonding atoms
How does a double bond effect a molecules geometery
the pi-bond locks the 2 carbon atoms in position and prevents them from rotating around the double bond
what is the shape around the double bond
the shape around each of the carbon atoms in the double bond is trigonal planar
why is the shape around a double bond the way it is
- 3 regions of electron density repel each other as far apart as possible, so the bond angle around each carbon atom is 120 degrees
what is steroisomerism
same molecular formula but different arrangement of atoms in space
what are the 2 types of stereoisomerism and when do they occur
there is E/Z isomerism and optical isomerism.
-E/Z isomerism only occurs in compounds with a c=c double bond,
-optical isomerism can occur in a much wider range of compounds, including alkanes with no functional groups
why does E/Z isomerism arise
stereoisomerism around double bonds arises because rotation about the double bond is restricted and the groups attached to each carbon atom are therefore fixed relative to each other
what causes the rigidity of double bonds
the reason for the rigidity is the position of the pi-bond’s electron density above and below the plane of the sigma-bond
what conditions have to be met for E/Z isomerism to occur
- C=C double bond
- different groups attached to each carbon atom of the double bond
what is cis-trans isomerism and when is it used
-cis-trans isomerism is the name commonly used to describe a special case of E/Z isomerism.
-in cis-trans isomers one of the attached groups on each carbon atom of the double bond must be hydrogen
match up the cis and trans to the corresponding E and Z
the cis isomer is the Z isomer
the trans isomer is the E isomer
how do you use cahn-ingold-prelog nomenclature
the atoms attached to each carbon atom in a double bond are given a priority based upon their atomic number
-if the groups of higher priority are on the same side of the double bond, the compound is the Z isomer
-if the groups of higher priority are diagonally placed across the double bond, the compound is the E isomer
whats the difference between E and Z isomers
The Z-isomer (zame) has the groups with priority together, either above or below the carbon, carbon double bond. The E-isomer occurs when the groups with priority are on opposite sides of the double bond.
how do you assign priority to atoms attached to double bond carbons
-examine the atoms attached directly to the carbon atoms of the double bond, the higher the atomic number, the higher the priority
-if the 2 atoms attached to a carbon atom in the double bond are the same, then you will need to find the first point of difference. The group which has the higher atomic number at the first point of difference is given the higher priority
are alkenes more or less reactive than alkanes and if so why
alkenes are much more reactive than alkanes because of the presence of the pi bond
what is the most common type of reaction that alkenes undergo
alkenes undergo addition reactions relatively easily
explain in terms of bonding why alkenes are able reactive
being on the outside of the double bond, the pi-bond are more exposed than the electron in the sigma-bond, pi-bonds breaks more readily allowing for reactions to occur
what are the most common addition reactions that alkenes undergo
-hydrogen in the presence of a nickel catalyst
-halogens
-hydrogen halides
-steam in the presence of an acid catalyst
explain the hydrogenation of alkenes
when an alkene is mixed with hydrogen and passed over a nickel catalyst at 423 K, an addition reaction takes place to form an alkane
-all C=C bonds react with hydrogen in this way