AQA Halogenoalkanes
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| Describe the mechanism for the Nucleophilic substitution of a HalogenoAlkane with COLD aqueous hydroxide ions | Present: show DELTA+/- on the C-X bond and lone PAIR on the OH-; attack: from the PAIR on OH- to the Cdelta+ (TOUCH-TOUCH); polarised C-X folds
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| Describe the mechanism for the Nucleophilic substitution of a HalogenoAlkane with cyanide ions | Present: show DELTA+/- on the C-X bond and lone PAIR on the CN- (the pair is on the carbon!); attack: from the PAIR on CN- to the Cdelta+ (TOUCH-TOUCH); polarised C-X folds
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| Describe the mechanism for the Nucleophilic substitution of a HalogenoAlkane with water | Present: show DELTA+/- and lone PAIR on the H2O; attack: from the PAIR on H2O to the Cdelta+ (TOUCH-TOUCH); polarised C-X folds; REWRITE; check charges: the O is (+) because it has 3 bonds; FURTHER: the O-H bond folds onto the Oxygen to release H+
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| Describe the mechanism for the Nucleophilic substitution of a HalogenoAlkane with ammonia | Present: show DELTA+/- and lone PAIR on the NH3; attack: from the PAIR on NH3 to the Cdelta+ (TOUCH-TOUCH); polarised C-X folds; REWRITE; check charges: the N is (+) because it has 4 bonds; FURTHER: the N-H bond folds onto the Nitrogen to release H+
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| Describe the mechanism for the Elimination of a HalogenoAlkane with HOT ethanolic hydroxide ions | Present: show DELTA+/- on the C-X bond and lone PAIR on the OH-; attack: from the PAIR on OH- to the H ADJACENT to the C-X (TOUCH-TOUCH); C-H folds to the MIDDLE of the C-C bond; polarised C-X folds: in TOTAL THREE CURLY ARROWS
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| What are the conditions for the formation of an AlkEne from a Halogenoalkane? | hot, ethanolic hydroxide
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| During the Elimination reaction, what is the role of hydroxide ions? | The hydroxide ions acts as a base
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| During the Nucleophilic Substitution reaction, what is the role of hydroxide ions? | The hydroxide ion acts as a nucleophile
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| What type of reaction is there with Ethanolic hydroxide ions? | Elimination
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| What type of reaction is there with aqueous hydroxide ions? | Nucleophilic substitution
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| Name CH3CCl2CH3 | 2,2DichloroPropane; did you remember to number EACH chloro?
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| Name (CH3)2CH2CHClCH3 | 2Chloro4MethylButane (or 4Chloro2MethylButane both are fine); the important part is that substituents should be in ALPHABETICAL order!
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| Write the structural formula for 2Bromo2Methylpropane | CH3-C(Br)(CH3)-CH3
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| Which bond C-X is the most polarised? C-Cl, C-Br or C-I? | C-Cl
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| Which bond C-X has the highest bond enthalpy? C-Cl, C-Br or C-I? Why? | C-Cl because the Cl has the smallest atomic radius so the bond C-X is shortest and short=strong
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| Describe the experiment to determine the kinetics (rate of) the hydrolysis of halogenoalkanes | Place Halogenoalkane in dil NaOH with Silver Nitrate; OH- replaces the halogen; this releases X- ion; the first precipitate to appear will show which C-X bond broke down first
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| During the experiment to determine the kinetics (rate of) the hydrolysis of halogenoalkanes, a yellow precipitate appears first. What is the formula of the precipitate? | yellow= AgI (LEARN)
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| During the experiment to determine the kinetics (rate of) the hydrolysis of halogenoalkanes, a yellow precipitate of AgI appears first. What can we conclude about what determines how fast the C-X breaks? | yellow ppt=IodIDE was liberated first=It is the C-I that breaks down first (and not the C-Cl, the most polarised bond as could have been thought)=therefore main factor is bond enthalpy
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| What is the colour of the Silver Chloride precipitate? | white
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| What is the colour of the Silver Bromide precipitate? | cream
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| What is the colour of the Silver Iodide precipitate? | yellow
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| What is the IONIC equation for the precipitation of Silver Iodide? | Ag+(aq) + I-(aq) --> AgI(s); there are not many IONIC equations that you will come across: this is one of them!
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| What is the IONIC equation for the reaction of chloride ions with silver nitrate? | Ag+(aq) + Cl-(aq) --> AgCl(s); remember the states! did you realise that the Nitrate is not involved (SNAP!)
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| What is the equation for the reaction of 2-Chlorobutane with aqueous sodium hydroxide? | Nucleophilic substitution; CH3-CH2-CHCl-CH3 + OH- ->CH3-CH2-CH(OH)-CH3 + Cl-; the Sodium does not take part (SNAP!)
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| What is the equation for the reaction of 2-Chlorobutane with ethanolic sodium hydroxide? | It is an elimination! CH3-CH2-CHCl-CH3 + OH- ->CH3-CH=CH-CH3 + HCl; OR CH3-CH2-CHCl-CH3 + OH- ->CH3-CH2-CH=CH2 + HCl; the Sodium does not take part (SNAP!); remember to check for E/Z isomers in the products
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| What is the equation for the reaction of 2-Chlorobutane with cyanide ions? | Nucleophilic substitution; CH3-CH2-CHCl-CH3 + CN- ->CH3-CH2-CH(CN)-CH3 + Cl-;
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| What is the equation for the reaction of 2-Chlorobutane with ammonia? | Nucleophilic substitution; CH3-CH2-CHCl-CH3 + NH3 ->CH3-CH2-CH(NH2)-CH3 + HCl;
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| Iodo Methane has the highest boiling point from FluoroMethane or Iodomethane. Explain why. | IodoMethane; both are molecular covalent; both have VdW and pd-pd; Iodine is less electronegative so weaker pd-pd but but more electrons on Iodo so stronger VdW; VdW outweighs pd-pd on this occasion
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| Name a nucleophile with a negative charge | OH- or CN-
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| Name a neutral nucleophile (no charge) | H2O or NH3
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| Name a nucleophile that increases the carbon chain by 1 unit (ie if you start with Bromoethane, that has 2 carbons, the product will have 3 carbons)? | CN- (cyanide)
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| What are the reaction conditions for the reaction of a Halogenoalkane with Ammonia? | in a sealed tube
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| How many organic products are formed during the elimination reaction of 2iodopentane? | Pent1Ene; E-Pent2Ene and Z-Pent2Ene; remember to always check for E/Z isomers when the product of the reaction are AlkEnes
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