5. Carbon-Carbon bond synthesis

Question 1

nucleophiles are

Answer 1

electron pair donors

they react with atoms that don’t have enough electrons (electrophiles)

Question 2

carbon carbon bond synthesis is used to

Answer 2

extend the carbon chain

Question 3

cyanide ions (CN-) are nucleophiles because they contain

Answer 3

a negativley charged carbon atom

Question 4

Cyanide ions (CN-) reac with carbon centres that have a

Answer 4

slight positive charge to create a new carbon-carbon bond

Question 5

when a Cyanide ion reacts with a carbon the compound initially produced is a

Answer 5

nitrile

Question 6

you can increase the length of a carbon chain by reacting

Answer 6

an organic compound that contains a slightly positive carbon centre with a cyanide reagent such as potassium cyanide KCN, sodium cyanide NaCN or hydrogen cyanide HCN

Question 7

cyanide ions CN- react with haloalkanes by what reaction

Answer 7

nucleophillic substitution

Question 8

why is the carbon electron deficient (electrophile) in a haloalkane

Answer 8

contain polar carbon-halogen bond

halogen generally more elctronegative than the carbon

Question 9

conditins needed for cyanide ions to react with haloalkanes forming a nitrile

Answer 9

reflux haloalkane with pottassium/sodium cyanide in ethanol

cyanide ions will react with haloalkane by nucleophilic substitution to form a nitrile (C2H5CN)

Question 10

how do you form a hydroxynitrile? RRCOHCN

Answer 10

mic a carbonyl compound (aldehyde/ketone) with hydrogen cyanide
cyanide ion reacts with positiv carbon centre to form a hydroxynitrile
nucleophillic addition

Question 11

why is it easy to convert a nitrile into a new functional group

Answer 11

nitrile groups are very reactive

Question 12

nitriles can be reduced to form

Answer 12

prmary amines

Question 13

how to reduce a nitrile to a primary amine

Answer 13

use lithium aluminium hydride LiAlH4 (strong reducing agent)
followed by dilute acid

Question 14

hydroxynitriles can be reduced to form

Answer 14

primary amine

Question 15

how to reduce hydroxynitrile to a primary amine

Answer 15

use lithium aluminium hydride LiAlH4 (strong reducing agent)
followed by dilute acid

Question 16

other reducing agents to reduce a nitrile or hydroxynitrile into a primary amine (other than lithium aluminium hydride )

Answer 16

sodium metal and ethanol

Question 17

in industry why aren’t LiAlH4 and sodium not used to reduce nitriles and hydroxynitriles (forming primary amines)

Answer 17

too expensive

Question 18

in indusrty what is used to reduce nitriles

Answer 18

hydrogen gas
metal catalyst (platinum or nickel)
high temperature and pressure (this is called catalytic hydrogenation)

Question 19

nitriles can be hydrolysed to form

Answer 19

carboxcylic acids

Question 20

how to hydrolyse a nitrile into a carboxylic acid

Answer 20

reflux nitrile in dilute HCl

Question 21

what kind of reaction forms carbon-carbon bonds with benzene rings

Answer 21

friedel-crafts reaction

Question 22

how to form a carbon-carbon bond between a benzene ring and a halogenated carbon

Answer 22

reflux benzene with a halogen carrier (e.g. AlCl3)

and either a haloalkane or an acyl chloride