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chemistry module 6 > nitriles + amines + amides + amino acids > Flashcards

nitriles + amines + amides + amino acids Flashcards

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1
Q

amine definition

A

an organic compound derived from ammonia

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2
Q

3 types of amines

A

primary - :NH2R
secondary - :NHR2
tertiary - :NR3

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3
Q

outline how amines can act as a base

A

they are able to accept a proton due to lone pair on N
however they are weak bases
acid + amine&raquo_space; ammonium salt

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4
Q

give the steps and reagents and conditions to produce aliphatic amines

A

reagents - haloalkane + excess NH3 - prevents further substitution of amine to form 2ndary/3iary amines
conditions - solvent is ethanol - this prevents substitution of haloalkane with water to form alcohols, also prevents formation of NH4+ which cannot act as a nucleophile
step 1 - ammonia + haloalkane&raquo_space; ammonium salt (RNH3+Cl-)
- here ammonia acts as a nucleophile due to its lone pair

step 2 - ammonium salt + NaOH&raquo_space; amine (RNH2) + salt + water

  • to form a secondary amine with these steps, replace the NH3 with a primary amine
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5
Q

give the steps and reagents and conditions used to produce aromatic amines

A

reagents - nitrobenzene + conc HCl + Sn + NaOH
conditions - reflux

step 1 - reduce nitrobenzene with conc HCl and Sn

step 2 - add excess NaOH
- produces phenylamine

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6
Q

why is it difficult to produce a pure amine product

A

primary amines still contain a lone pair of electrons on the N so are able to produce secondary amines, this is again the case for secondary and tertiary amines so it is very difficult to make a pure amine product

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7
Q

nitrile definition

A

an organic compound with a C≡N group

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8
Q

give the reagents and conditions and mechanism to form a hydroxynitrile from a carbonyl - chain elongation

A

reagents - NaCN + H2SO4 to form HCN in situ - HCN can be used in equations
conditions - aqueous

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9
Q

why is HCN alone not used as a reagent

A

HCN is a colourless + poisonous liquid, and is also very volatile as it boils slightly above room temp, so it cannot be safely used in a lab

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10
Q

give the reagents and conditions to go from a haloalkane to a nitrile - chain elongation

A

reagents - NaCN + H2SO4 to form HCN in situ - HCN can be used in equations
conditions - aqueous

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11
Q

give the reagents and conditions to go from a nitrile to an amine - reduction

A

reagent - H2
conditions - Ni catalyst

  • NaBH4 can also be used, but H2/Ni is better
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12
Q

give the steps and reagents and conditions to go from a nitrile to a carboxylic acid - acid hydrolysis

A

reagents - acid e.g. H2SO4
conditions - aqueous

step 1 - nitrile + water&raquo_space; amide
R-CN + H2O&raquo_space; R-CO-NH2
(forms C=O bond)

step 2 - R-CO-NH2 + H2O&raquo_space; R-CO-ONH4

step 3 - R-CO-ONH4 + H+&raquo_space; R-COOH + NH4

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13
Q

amino acid definition

A

an organic compound that contains both NH2 and COOH functional groups

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14
Q

how many common amino acids are found in the body + what type of amino acid are they

A

20
they are alpha amino acids

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15
Q

alpha amino acid definition

A

an amino acid where the amine and carboxyl group are attached to the same carbon

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16
Q

amphoteric definition

A

a compound which is able to react as both an acid and a base

17
Q

what makes amino acids amphoteric

A

they have an NH2 group which can act as a base, and a COOH group which can act as an acid

18
Q

what is formed when amino acids are reacted with acids

A

NH2 group reacts to form an ammonium salt

19
Q

what is formed when amino acids are reacted with bases

A

COOH group reacts to form carboxylate salts

20
Q

what is formed when amino acids are reacted with alcohols

A

the COOH group reacts to form an ester - if heated under reflux with conc H2SO4

the NH2 group would also be protonated to form NH3+

21
Q

zwitterion definition

A

this is formed when the H on the COOH group of an amino acid dissociates and associates onto the NH2 group, forming both COO- and NH3+ ions

22
Q

isoelectric point definition

A

the point at which a zwitterion is formed - unique for each amino acid

23
Q

how to name amino acids e.g. glycine - simplest one, R group = H

A

the carboxyl group takes priority so NH2 group will always be at position 2 in alpha amino acids
e.g. glycine - NH2-CH2-COOH
2-amino ethanoic acid

24
Q

why do many amino acids display optical isomerism + name 1 exception

A

on most amino acids, the alpha carbon is bonded to 4 different groups, being NH2, COOH, H and R group
this means there is a chiral carbon, therefore can display optical isomerism

one exception is glycine, as its R group is H, there aren’t 4 different groups bonded to the alpha carbon, so no chiral centre

25
Q

state the general formula for an amino acid

A

H2NCH(R)COOH

26
Q

chiral centre definition

A

an atom bonded to all different groups

27
Q

amide definition

A

organic compounds with an amine group directly bonded with a carbonyl group

28
Q

how are primary amides formed

A

acyl chloride/acid anhydride + ammonia/amine&raquo_space; amide + salt/carboxylic acid

29
Q

3 types of amide

A

primary - R-CO-NH2
secondary - R-CO-NHR
tertiary - R-CO-NR2

30
Q

how are secondary amides formed

A

acyl chloride/acid anhydride + primary amide&raquo_space; secondary amide + salt/carboxylic acid

31
Q

by what mechanism are amides formed

A

nucleophilic addition elimination

32
Q

optical isomerism definition

A

molecules that are nonsuperimposable mirror images of eachother

33
Q

what must a compound contain to display optical isomerism

A

a chiral centre

34
Q

racemic mixture definition

A

a mixture containing 50% of each optical isomer
- this means there is only 1 chiral centre

35
Q

what are some properties of optical isomers

A

optical isomers are able to rotate plane-polarised light in different directions - each optical isomer rotates it in a different direction, either clockwise or anticlockwise

as racemic mixtures contain equal proportions of each optical isomer, this has no effect on plane-polarised light

chemistry module 6 (5 decks)

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