C Unit 2.6 Halogenoalkanes Revamp Flashcards
Define halogenoalkane
(3-way)
- Homologous series (Similar to Alkanes/Alkenes)
- Which 1/more of H atoms replaced
- by a halogen
How do we turn a halogenoalkane from saturated to unsaturated compounds?
(+ what it gives us)
Undergoing an elimination reaction
+ separating the halogen
How are halogenoalkanes able to undergo an elimination reaction?
(2-way)
- Hydrogen halides are acidic
- Therefore can be removed using an alkali
What is used to have the halogenoalkane to undergo an elimination reaction?
NaOH dissolved in Ethanol
Draw 1-bromopropane converted into propene and HBr
Stage is yours y’all
How can halogenoalkanes form more than 1 product when undergoing an elimination reaction?
For only unsymmetrical halogenoalkanes
Draw 2-bromobutane and the conversion of 2 products?
Stage is yours D:
Define nucleophile
(3-way)
- Atom/group of atoms
- That has an electron pair
- That can be donated to an e- deficient centre
The significance of halogenoalkanes having a permanent dipole?
(3-way)
- e- deficient carbons can undergo
- nucleophilic attack leading to
- nucleophilic substitution
For any mechanism, what are 4 things that are needed?
- Lone pairs
- Dipoles
- Charges
- Curly arrows
Draw the mechanism for the nucleophilic substitution of 1-chloropropane by sodium hydroxide
All yours.
Also, spectator ion is totally optional but aye, isn’t it nicer to clarify things?
What is the rate of nucleophilic substitution factored on?
(2 things)
- Strength of the carbon-halogen (C-X) bond (bond enthalpy)
- How strongly they attract electrons? (bond polarity)
Relationship between reactivity, strength of bond, and rate?
(3-way)
- More reactive the halogen,
- Stronger the bond will be,
- The longer the reaction will take
Hence, what are the bond strengths of carbon-halogen bonds for the 4 halogens?
(2 points)
- Fluorine strongest (More electronegative)
- Downwards, iodine the weakest (Least electronegative)
How come the carbon-fluorine bond may get ignored?
(3 points)
- Very strong
- Greatest polarity
- May be very unreactive
Hence show rates of reaction from slowest to fastest of halogenoalkanes?
RCl > RBr > RI
The purpose of hydrolysing halogenoalkanes?
(Adding water)
(2 things… kinda check up but still serves the purpose)
- Produce alcohols ig? (+ hydroxonium ion)
- And to test if it’s rlly a halogenoalkane???
Why is nucleophilic substitution slow for hydrolysis of halogenoalkanes?
(2 things)
- Water not very good nucleophile
- Lacks full negative charge (in comparison to -OH)
Hence, how to speed up nucleophilic substitution for hydrolysis of halogenoalkanes?
Use Sodium Hydroxide (NaOH)
Then, draw mechanism for the nucleophilic substitution of 1-chloropropane with water
Allll yours pal
Therefore, the real way to test for halogenoalkanes?
+ brief explanation
- Using silver nitrate (AgNO3)
- Observing peculiar ppts
What would happen if we used just NaOH insteada water against halogenoalkanes?
Hence a counter?
- Interference of results (totally different outcome)
- Neutralise alkali by addition of nitric acid (NO3)
Chloride w/ Ag+ observation?
White ppt
Chloride w/ Ag+ **addition of NH3** observation?
Ppt dissolves
Bromide w/ Ag+ observation?
Cream ppt
Bromide w/ Ag+ addition of NH3 observation?
(2-way)
- If NH3 is concentrated
- Ppt dissolves (…. otherwise….)
Iodide w/ Ag+ observation?
Yellow ppt
Iodide w/ Ag+ addition of NH3 observation?
No change
What are CFCs (chlorofluorocarbons)?
(2-way)
- Halogenoalkane molecules where
- all H atoms replaced with F/C atoms
Describe CFCs?
(3 points)
- Non-flammable
- Not very toxic
- Large number of uses
Say some uses of CFCs?
(At least know one, like ig it’s deep)
- Refrigerants
- Propellants for aerosols
- Generating foamed plastics (e.g. expanded polystyrene/polyurethane foam)
- Solvents for dry cleaning/general degreasing purposes
- Anaesthetics
The big 3 tragedies of CFCs?
- Largely responsible for destroying ozone layer
- Contributed to global warming (Not stronger than CO2)
- Indirect cause of skin cancer (Ozone holes)
What caused CFCs to destroying ozone layer?
(5-way)
- At high atmosphere
- Carbon-chlorine bonds break giving
- Chlorine free radicals
- Which destroy ozone layer
- 1 ˙Cl destroying 1000s of ozone molecules
What are ozone holes?
(3-way)
- Marked decreases in concentration of
- ozone in the ozone layer above
- north and south poles
Tragedy of decrease of ozone concentration?
(2-way)
- Medium to high energy UV radiation
- reached surface of earth
What can medium to high energy UV radiation cause?
(Likewise to previous y’alls in terms of acknowledging)
- Sunburn
- Skin cancers
- Eye cataracts
- Decreased immune response
- Plant damage
- Polymer decomposition
What was the only truest way to stop ozone destruction by CFCs?
… Prevent release of substance
How come C-Cl bond was the main radical attacker than other bonds (C-F/C-H)
(2-way)
- More difficult to break C-H/C-F
- Hence C-Cl pronounced the HIGHEST DPS (main radical)
Define reflux?
(2-way)
- Heating a reaction mixture to boiling
- Process of evaporation and condensation
How would we prepare alcohols from halogenoalkanes?
(3-way)
- Nucleophilic substitution
- w/ Aq sodium hydroxide
- when heated to reflux
Quick alternate method insteada reflux?
Distillation
Explain how the reflux works
(6 step by steps w/ 1 obviously being 2-way)
- Rxn mixture heated
- Liquids evaporate
- Vapour rises up through condenser
- Condenser has cold-water jacket
- which’ll cool vapour to a liquid
- Dripping back into rxn mixture
Ig then a simple summarisation of reflux then?
(3-way)
- A continuous process of evaporation and
- condensation taking place
- without loss of product
The least we can do, list the apparatus and chemicals for reflux of halogenoalkanes?
(Maybe know one? Or acknowledge, I’m unsure.. hence major check-up)
Apparatus:
- Round-bottom flask
- Reflux condenser
- Heat source (water bath or heating mantle)
- Anti-bumping granules (to prevent violent boiling)
- Clamps and stand
Chemicals:
- Halogenoalkane (e.g., 1-bromobutane)
- Aqueous sodium hydroxide (NaOH)
- Ethanol (as a co-solvent, because NaOH is not very soluble in halogenoalkanes)
Almost there
Thank the past self future self