unit 2a: synthesis Flashcards
homolytic fission
involves the bond breaking evenly, meaning one electron from the shared pair in the bond goes into each atom, usually occurs in non-polar bonds
free radicals
the result of homolytic fission, highly reactive species with unpaired electrons
heterolytic fission
involves the bond breaking unevenly- with one atom getting both electrons from the bond and the other getting none, usually occurs in polar bonds
result of homolytic fission
free radicals
result of heterolytic fission
positive and negative ions
curly arrow notation
used to show the movement of electrons
a single headed arrow
represents the movement of a single electron
a double headed arrow
represents the movement of a pair of electrons
two categories of attacking groups
electrophiles and nucleophiles
electrophiles
atoms or groups of atoms which are deficient in electrons, usually have a positive or partial positive charge and are able to accept electrons, they are attracted to a region of negative charge or groups that can donate electrons
electrophile examples
Na^+, Mg^2+, NH4^+, NO2^+
carbocations
positive carbon based ions
nucleophiles
atoms or groups of atoms which are rich in electrons, usually have a negative or partial negative charge or lone pairs and are able to donate electrons, they are attracted to a region of positive charge or groups that can accept electrons
nucleophile examples
Cl^-, CN^-, H2O, C=C, OH^-, NH3
elimination reactions
when atoms are removed from a molecule and a double bond is formed, they are the opposite of addition reactions
substitution
when an atom or functional group is replaced by a different atom or functional group
three types of substitution
free radical, electrophilic, nucleophilic
free radical substitution
when UV light is used to trigger a free radical chain reaction
electrophilic substitution
when an electrophile attacks a compound
nucleophilic substitution
when a nucleophile attacks a compound
monohaloalkanes can be made by
reacting alkanes with a halogen (free radical substitution), reacting a hydrogen halide with an alkene (addition), synthesised from alcohols
addition
a reaction where a small molecule adds onto an unsaturated molecule by reacting with the C=C double bond
condensation
a reaction where two molecules combine to form a larger molecule, by eliminating a smaller molecule
hydrolysis
a reaction where a molecule is broken down, by reaction with water
oxidation
oxidation causes and increase in the oxygen to hydrogen ratio
reduction
reduction causes a decrease in the oxygen to hydrogen ratio
neutralisation
a reaction between an acid and a base, most examples involve carboxylic acids reacting with bases, e.g. alkaline hydrolysis of fats/oils using sodium hydroxide in the making of soaps
haloalkanes and nucleophilic substitution
the carbon - halogen bond is highly polar, the carbon is partially positive so it can be attacked by a nucleophile
the two nucleophilic substitution mechanisms
Sn1, Sn2
Sn2 is undergone by
primary and secondary haloalkanes
process of Sn2
the rate determining step (two molecules), transition state/activated complex, final molecule
Sn1 is undergone by
tertiary haloalkanes
process of Sn1
rate determining step (one molecule), final molecule
reasons for primary and secondary undergoing Sn2 and tertiary undergoing Sn1
steric hindrance, carbocation stability
steric hindrance
in primary and secondary haloalkanes there is space for the nucleophile to attack the carbon, in tertiary there is not