Lesson 3.3.11.3
3.3.11.3 Nucleophilic properties Quiz: AQA Chemistry, Unit 3
20 questions
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Lesson 3.3.11.3, Nucleophilic properties: 20 multiple choice questions for the AQA Chemistry (7405), Unit 3: Organic chemistry, written with Revision Ninja.
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The 20 questions
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Why are amines nucleophiles?
- Their nitrogen lone pair is donated to an electron-deficient carbon atom
- They always lose a proton to form an acid, which makes them react with carbon
- They contain a carbon-carbon double bond that adds to electron-rich centres
- They carry a full positive charge on nitrogen, so they attract nucleophiles
-
What is the main first product when excess ammonia reacts with a halogenoalkane?
- A quaternary ammonium salt
- A tertiary amine
- An amide
- A primary amine
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Which species is a quaternary ammonium salt?
- A nitrogen atom with one alkyl group and a lone pair, which can form a salt
- A nitrogen atom bonded to four alkyl groups with a positive charge
- A nitrogen atom in a benzene ring, which is an aromatic quaternary centre in the ring
- A carbon atom bonded to four hydrogen atoms, which is the usual nucleophile in substitution
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What are quaternary ammonium salts used for in the specification?
- Dye intermediates
- Polyalkene manufacture
- Biodiesel fuel
- Cationic surfactants
-
What product forms when a primary amine such as methylamine reacts with ethanoyl chloride?
- Methyl ethanoate
- Ethanamide
- Ethanoic acid
- N-methylethanamide
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What is the first step when ammonia attacks bromoethane?
- The lone pair on nitrogen attacks the carbon bonded to bromine
- Bromine atom attacks the nitrogen atom, pulling the lone pair towards the halogen
- A proton is removed from the nitrogen, forming an imine that then reacts with bromine
- The C-C bond breaks to form ethene, which then adds ammonia across the double bond
-
What is the product when ethylamine reacts with bromoethane?
- Diethylamine
- Tetraethylammonium bromide
- Triethylamine
- Ethanamine
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What is the product when triethylamine reacts with excess bromoethane?
- Tetraethylammonium bromide, which forms directly from one bromoethane and ammonia
- Ethylamine, which is simply left over unchanged because it is a poor nucleophile
- Tetraethylammonium bromide
- Ethanamide, which forms when bromoethane is oxidised by the excess ammonia present
-
Why is ethylamine a better nucleophile than phenylamine toward bromoethane?
- Ethylamine contains a triple bond that makes it react with bromoethane by an addition mechanism
- Its lone pair is more available because the ethyl group is electron-donating and the lone pair is not delocalised into a ring
- Bromoethane reacts only with phenylamine and never with the alkylamine present in the mixture
- Phenylamine contains no lone pair on nitrogen, so it cannot act as a nucleophile at all here
-
Why is excess ammonia used to make a primary amine from a halogenoalkane?
- It converts the halogenoalkane into an alkene by elimination before any amine has time to form
- It removes the bromide ion from the solution by precipitating it as insoluble silver bromide
- It makes the halogenoalkane more likely to meet a stronger nucleophile than the amine, so substitution is increased
- It makes collision with the halogenoalkane more likely than with the product amine, reducing further substitution
-
Which species is the nucleophile in the reaction of ammonia with bromoethane?
- The hydrogen atoms of ammonia, which are removed by the halogenoalkane to form a salt
- The bromine atom of bromoethane, which is the nucleophile that attacks the amine
- The lone pair on the nitrogen atom of NH3
- The carbon atom of bromoethane, which carries a lone pair that it donates to ammonia
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What is the leaving species in the addition-elimination reaction of ammonia with ethanoyl chloride?
- Chloride ion, Cl-
- Hydride ion, H-
- Ammonium ion, NH4+
- Hydroxide ion, OH-
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Why is ethanoyl chloride used rather than ethanoic acid to make an amide?
- The acyl chloride carbonyl carbon is more electrophilic and reacts readily under mild conditions
- Ethanoic acid cannot form any bond to nitrogen, so it cannot react with the amine
- Ethanoyl chloride contains a nitrogen atom that makes it react with amines readily
- Ethanoic acid is a gas at room temperature, so it cannot be mixed with the amine
-
What happens to the HCl formed when a primary amine reacts with an acyl chloride?
- It is converted into methane
- It is removed by reaction with excess amine to form a salt
- It remains dissolved and acts as the nucleophile
- It is released as a gas and changes the amide to an ester
-
Why are quaternary ammonium salts effective cationic surfactants?
- They are anions that repel all surfaces and so prevent any cleaning action in a detergent solution
- Their negative head is attracted to positive surfaces while their hydrophobic alkyl tails repel grease
- Their positive head is attracted to negative surfaces while their hydrophobic alkyl tails can interact with grease
- They are neutral molecules that dissolve in oil only and do not affect the surfaces they touch
-
Which statement about quaternary ammonium compounds is correct?
- The nitrogen carries a permanent positive charge because it has four bonds to alkyl groups
- The nitrogen carries a negative charge when four alkyl groups are present
- They are always gases at room temperature
- The nitrogen has a lone pair that makes the salt a base
-
Which species is the electrophile in the addition-elimination reaction of an amine with an acyl chloride?
- The carbonyl carbon of the acyl chloride
- The hydrogen atom of the amine
- The nitrogen lone pair of the amine
- The chlorine atom of the acyl chloride
-
What is the mass of ethylamine (C2H7N, Mr 45) formed from 0.1 mol of bromoethane with excess ammonia?
- 4.5 g
- 45 g
- 2.25 g
- 9.0 g
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What happens when a primary amine reacts with an acid anhydride?
- It forms an ester and hydrogen chloride, as a condensation product of the amine
- It forms an N-substituted amide and a carboxylic acid by-product
- It forms a nitrile and water, because the amine is dehydrated by the anhydride
- It forms a quaternary salt only, because the amine is always fully alkylated
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Which statement about the product of a primary amine with an acyl chloride is correct?
- It is an alkene
- It is a carboxylic acid with no nitrogen
- It is an N-substituted amide
- It is a quaternary ammonium salt
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