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AQA A1HalogenoAlkane

AQA Halogenoalkanes

QuestionAnswer
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
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
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+
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+
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
What are the conditions for the formation of an AlkEne from a Halogenoalkane? hot, ethanolic hydroxide
During the Elimination reaction, what is the role of hydroxide ions? The hydroxide ions acts as a base
During the Nucleophilic Substitution reaction, what is the role of hydroxide ions? The hydroxide ion acts as a nucleophile
What type of reaction is there with Ethanolic hydroxide ions? Elimination
What type of reaction is there with aqueous hydroxide ions? Nucleophilic substitution
Name CH3CCl2CH3 2,2DichloroPropane; did you remember to number EACH chloro?
Name (CH3)2CH2CHClCH3 2Chloro4MethylButane (or 4Chloro2MethylButane both are fine); the important part is that substituents should be in ALPHABETICAL order!
Write the structural formula for 2Bromo2Methylpropane CH3-C(Br)(CH3)-CH3
Which bond C-X is the most polarised? C-Cl, C-Br or C-I? C-Cl
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
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
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)
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
What is the colour of the Silver Chloride precipitate? white
What is the colour of the Silver Bromide precipitate? cream
What is the colour of the Silver Iodide precipitate? yellow
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!
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!)
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!)
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
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-;
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;
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
Name a nucleophile with a negative charge OH- or CN-
Name a neutral nucleophile (no charge) H2O or NH3
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)
What are the reaction conditions for the reaction of a Halogenoalkane with Ammonia? in a sealed tube
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
Created by: UrsulineChem