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Advanced A Level Organic Chemistry: Reaction mechanisms - hydrolysis of halogenoalkanes
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ALL advanced revision notes on halogenoalkanes (haloalkanes) All my advanced A level organic chemistry notes Index of GCSE level oil and basic organic chemistry notes Use your mobile phone or ipad etc. in 'landscape' style This is a BIG website, you need to take time to explore it [SEARCH BOX] A Level Revision Notes PART 10 Summary of organic reaction mechanisms - Help in revising organic chemistry - A mechanistic introduction to organic chemistry and explanations of different types of organic reactions Part 10.4 Halogenoalkanes - Reaction with water and hydroxide ion - hydrolysis
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10.4 HALOGENOALKANES (old names 'haloalkanes' or 'alkyl halides') 10.4.1 Introduction to halogenoalkane reactivity
Remember: A neutral or negative nucleophile, Nuc: or Nuc:-, is an electron pair donor that can attack an electron deficient partially/wholly positive carbon atom to form a new C-Nuc bond.
10.4.2 Nucleophilic substitution of halogenoalkane by hydroxide ion (hydrolysis with OH-)
SN1 mechanism mechanism 1 - nucleophilic substitution of a halogenoalkane by hydroxide ion (SN1 'unimolecular' via carbocation)
SN2 mechanism Three diagram 'styles' are shown below for the SN2 bimolecular mechanism that does NOT involve a carbocation.
style (a)
mechanism 2 - nucleophilic substitution of a halogenoalkane by hydroxide ion (SN2 'bimolecular') simplest representation of the one step mechanism
style (b)
mechanism 34 - nucleophilic substitution of a halogenoalkane by hydroxide ion (SN2 'bimolecular') showing the intermediate transition state ('activated complex')
style
(c)
mechanism 33 - nucleophilic substitution of a halogenoalkane by hydroxide ion (SN2 'bimolecular') showing the intermediate transition state ('activated complex') in a 3D representation - note the inversion of the crucial carbon atom, if its an asymmetric carbon atom you don't produce the optical (R/S) stereoisomers you might expect!
Also read the FURTHER COMMENTS for this reaction 10.4.3 Nucleophilic substitution of halogenoalkane by direct hydrolysis with water
mechanism 10 - nucleophilic substitution of a halogenoalkane by water (SN1 unimolecular via carbocation)
mechanism 35 nucleophilic substitution of a halogenoalkane by water (SN2 bimolecular)
Further notes 10.4.4 FURTHER comments on the hydrolysis of halogenoalkanes with water or alkaline hydroxides
Reaction progress profile for the SN1 hydrolysis of halogenoalkanes with the hydroxide nucleophile OH- e.g. for mechanism diagram 1 above, note that step 1 is the unimolecular rate determining step, with the largest activation energy Ea1.
Reaction progress profile for the SN2 hydrolysis of halogenoalkanes with the hydroxide nucleophile OH- e.g. for mechanism diagram 2 above, note that step 1 is the bimolecular rate determining step, single activation energy of Ea.
SN1 hydrolysis of a halogenoalkane with H2O (e.g. for mechanism 10 above, note the triple hump!) Step 1 is the unimolecular rate determining step, with the largest activation energy Ea1
Reaction profile 45b for the SN2 hydrolysis of halogenoalkanes directly with water (for mechanism diagram 35 above) Step 1 is the bimolecular rate determining step, with the largest activation energy Ea1.
10.4.3 The nucleophilic substitution of halogenoalkane by cyanide ion now on separate page 10.4.5 The elimination of hydrogen bromide from a bromoalkane now on separate page COMPLETE MECHANISM and Organic Synthesis INDEX (so far!)
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Edexcel A level chemistry notes on hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for OCR A level chemistry notes WJEC A level chemistry notes on hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes CCEA/CEA A level chemistry notes on hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for university entrance examinations keywords phrases: reaction conditions formula intermediates organic chemistry reaction mechanisms nucleophilic substitution R3C-X + OH- ==> R3C-OH + X- R3C-X + 2H2O ==> R3C-OH + X- + H3O+ C6H5CH2Cl + NaOH ==> C6H5CH2OH + NaCl ClC6H4CH3 + NaOH ==> HOC6H4CH3 + NaCl (CH3)3CBr > (CH3)2CHBr > CH3CH2Br > CH3Br (CH3)3C+ > (CH3)2CH+ > CH3CH2+ > CH3+ hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for AQA AS chemistry, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for Edexcel A level AS chemistry, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for A level OCR AS chemistry A, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for OCR Salters AS chemistry B, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for AQA A level chemistry, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for A level Edexcel A level chemistry, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for OCR A level chemistry A, hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for A level OCR Salters A level chemistry B hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for US Honours grade 11 grade 12 hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for pre-university chemistry courses pre-university A level revision notes for hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes A level guide notes on hydrolysis 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A level chemistry notes on hydrolysis mechanism hydroxide ion or water with haloalkanes halogenoalkanes for university entrance examinations how do you explain the reactivity of xyz towards nucleophiles like the hydroxide ion? how do bond strength and bond polarity affect the reactivity of xyz?, give the mechanism of hydrolysis of xyz with sodium hydroxide, describe the difference between an unimolecular SN1 mechanism and a bimolecular SN2 mechanism, why can't aryl chlorides like chlorobenzene be readily hydrolysed by sodium hydroxide solution? how does the relative stability of carbocations affect the rate of nucleophilic attack on xyz? how does the stability of carbocations affect the mechanistic steps of the hydrolysis of xyz with sodium hydroxide? |
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