Carbon-Carbon Bond Formation Flashcards
What is the nitrile group in nitriles?
the organic functionally group CN
What is propane nitrile?
CH3CH2CN
What can be reacted with haloalkanes to form nitriles?
Reagents like sodium cyanide and or potassium in ethanol
R-X +NaCN → RCN + NaX where R is a carbon chain and X is a halogen
Na + not featured in overall equation
What do nitriles form by?
nucleophilic substitution- arrow pointing from cn at c, arrow from bond to halogen
How can aldehydes and ketone be reacted to with HCN or other metal cyanides in the presence of H+?
via a nucleophilic addition
What is the correct mechanism for the reaction of CN- with haloalkanes?
nucleophilic substitution
What is the correct mechanism for the reaction of CN- with carbonyl compounds?
nucleophilic addition
How can nitriles be reduced to form amines?
using hydrogen in the presence of a nickel catalyst
What are do nitriles produce when being reduced?
primary anime
For the reduction of every nitrile, what is needed?
2 lots of H2 and a nickel catalyst
What do nitriles undergo hydrolysis to form? and how?
carboxylic acids by heating in dilute aqueous acid
What is the first thing I must do when calculating % yield?
moles
What is a way of increasing the number of atoms in an aromatic compound?
Alkylation
What is alkylation?
This is a way of attaching an alkyl group from a haloalkane directly to a benzene
ring
What mechanism does alkylation of a benzene ring follow?
electrophilic substitution
What is the catalyst for the alkylation of benzene?
AlCl3
How are hydroxy nitriles formed?
Aldehydes and ketones can be reacted with hydrogen cyanide (HCN)or other
metal cyanides (in the presence of H+) via a nucleophilic addition mechanism. The cyanide ion acts in exactly the same way as the hydride ion.
Outline the mechanism for the reaction of ethanal with KCN(aq)/H2SO4(aq).
-arrow from lone pair on :CN+ to C
double bond breaks on O
CN- on c
lone pair on O- points to H+
o- becomes oh
how are nitriles reduced?
can be reduced to form amines using hydrogen, in the presence of a nickel
catalyst-
triple bond is broken and becomes NH2
any double bond is broken and H is added
What do nitriles undergo hydrolysis to form?
carboxylic acids by heating in dilute aqueous acid, eg HCl(aq).
For example:
CH3CH2CN + 2H2O + HCl →CH3CH2COOH + NH4Cl
West are carbon-carbon bonds in benzene ring?
This is a way of increasing the number of carbon atoms in an aromatic compound.
what is alkylation?
This is a way of attaching an alkyl group from a haloalkane directly to a benzene
ring.
what happens in alkylation?
Alkylation of a benzene ring follows an Electrophilic Substitution mechanism. The catalyst is typically aluminium chloride, formula AlCl3
