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