Electrophilic Addition

Electrophilic Addition
Alkenes and Electrophilic Addition New Way Chemistry for Hong Kong A-Level 3A

Preparation of Alkenes
New Way Chemistry for Hong Kong A-Level 3A

New Way Chemistry for Hong Kong A-Level 3A
A. Industrial preparation Cracking Prepared by the cracking of alkanes of high molecular masses Give alkenes of low molecular masses New Way Chemistry for Hong Kong A-Level 3A

Cracking e.g. 2CH3CH3  CH2 = CH2 + 2CH4 600 oC 2CH3CH2CH3  CH3CH = CH2 + CH2 = CH2 + CH4 + H2 600 oC New Way Chemistry for Hong Kong A-Level 3A

B. Synthetic preparation Elimination Reactions Involve removal of atoms or groups of atoms from adjacent carbon atoms in the reactant molecule Formation of a double bond between carbon atoms New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols Removal of a water molecule from a reactant molecule By heating the alcohols in the presence of a dehydrating agent. E.g. Alumina(Al2O3), conc. H2SO4, conc. H3PO4 Give alkenes and water as the products New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols Experimental conditions (i.e. temperature and concentration of concentrated sulphuric acid) is closely related to the structure of the individual alcohol. New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols Primary alcohols generally required concentrated sulphuric acid and a relatively high temperature New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols Secondary alcohols are intermediate in reactivity Tertiary alcohols dehydrate under mild conditions (moderate temperature and dilute sulphuric acid) New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols The relative ease of dehydration of alcohols generally decreases in the order: Tertiary alcohol Secondary alcohol > Primary alcohol New Way Chemistry for Hong Kong A-Level 3A

Intramolecular vs intermolecular Substitution New Way Chemistry for Hong Kong A-Level 3A

Intramolecular dehydration is favoured at higher temperatures because it involves breaking of strong C – H bonds. New Way Chemistry for Hong Kong A-Level 3A

Q.29(a) New Way Chemistry for Hong Kong A-Level 3A

Q.29(b) New Way Chemistry for Hong Kong A-Level 3A

Q.29(c)  New Way Chemistry for Hong Kong A-Level 3A

1. Intramolecular Dehydration of Alcohols Secondary and tertiary alcohols may dehydrate to give a mixture of alkenes The more highly substituted alkene is formed as the major product New Way Chemistry for Hong Kong A-Level 3A

2. Dehydrohalogenation of haloalkanes Elimination of a hydrogen halide molecule from a haloalkane By heating the haloalkane in an alcoholic solution of KOH New Way Chemistry for Hong Kong A-Level 3A

C2H5OH is a co-solvent for both RX and OH New Way Chemistry for Hong Kong A-Level 3A

2. Dehyhalogenation of haloalkanes e.g. New Way Chemistry for Hong Kong A-Level 3A

2. Dehyhalogenation of haloalkanes Dehydrohalogenation of secondary or tertiary haloalkanes can take place in more than one way A mixture of alkenes is formed New Way Chemistry for Hong Kong A-Level 3A

Q.30(a) New Way Chemistry for Hong Kong A-Level 3A

Q.30(b) New Way Chemistry for Hong Kong A-Level 3A

2. Dehyhalogenation of haloalkanes The ease of dehydrohalogenation of haloalkanes decreases in the order: Tertiary haloalkane Secondary haloalkane > Primary haloalkane > New Way Chemistry for Hong Kong A-Level 3A

The relative stabilities of alkenes decrease in the order: New Way Chemistry for Hong Kong A-Level 3A

Relative Stability of Alkenes in Terms of Enthalpy Changes of Hydrogenation Hydrogenation of alkenes is exothermic From enthalpy changes of hydrogenation  predict the relative stabilities of alkenes New Way Chemistry for Hong Kong A-Level 3A

Enthalpy changes of hydrogenation of but-1-ene, cis-but-2-ene and trans-but-2-ene New Way Chemistry for Hong Kong A-Level 3A

Relative Stability of Alkenes in Terms of Enthalpy Changes of Hydrogenation The pattern of the relative stabilities of alkenes determined from the enthalpy changes of hydrogenation: New Way Chemistry for Hong Kong A-Level 3A

Addition Reactions Hydrogenation of alkynes Alkenes can be prepared by hydrogenation of alkynes  Depend on the conditions and the catalyst employed New Way Chemistry for Hong Kong A-Level 3A

Hydrogenation Lindlar’s catalyst is metallic palladium(Pd) deposited on calcium carbonate  further hydrogenation of the alkenes formed can be prevented New Way Chemistry for Hong Kong A-Level 3A

Reactions of Alkenes An Introduction New Way Chemistry for Hong Kong A-Level 3A

Alkenes are more reactive than alkanes Undergoes addition reaction rather than substitution New Way Chemistry for Hong Kong A-Level 3A

Presence of C=C double bond C=C double bond is made up of a  bond and a  bond Addition reactions only involve breaking of weaker  bonds of alkenes New Way Chemistry for Hong Kong A-Level 3A

The electrons of the  bond are  diffuse in shape  less firmly held by the bonding carbon nuclei Susceptible to the attack by electrophiles New Way Chemistry for Hong Kong A-Level 3A

Electrophiles : - Electron-deficient species Attack electron-rich center e.g. C=C bond Examples : Cations : H+, Br+, R+,… (lead to heterolysis) Free radicals : H, Cl, R,…(lead to homolysis) New Way Chemistry for Hong Kong A-Level 3A

Nucleophiles : - Electron-rich species Attack electron-deficient site e.g. carbonyl carbon, C=O Examples : anions : OH, Br, RO,… molecules : H2O, ROH, NH3 All have lone pairs for donating to the reaction sites All lead to heterolytic fissions New Way Chemistry for Hong Kong A-Level 3A

Reactions of Alkenes Examples New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Alkenes react with hydrogen in the presence of metal catalysts (e.g. Ni, Pd, Pt) to give alkanes Lower temperatures can be used with Pd or Pt New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation e.g. cis-addition, refer to notes on ‘chemical kinetics’, pp.36-37) New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Under mild conditions, C=O and benzene ring are unaffected. New Way Chemistry for Hong Kong A-Level 3A

Q.31 New Way Chemistry for Hong Kong A-Level 3A

A / B New Way Chemistry for Hong Kong A-Level 3A

* * New Way Chemistry for Hong Kong A-Level 3A

Application : - hardening of plant oils Plant oil (polyunsaturated liquid with low m.p.) Partial hydrogenation Margarine (soft unsat’d solid with higher m.p.) Complete hydrogenation Animal fat (hard sat’d solid with still higher m.p.) New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Fats and oils are organic compounds called triglycerides  triesters formed from glycerol and carboxylic acids of long carbon chains New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Saturated fats  solids at room temp  usually come from animal sources  long carbon chains are zig-zag and easily packed New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Unsaturated oils  liquids at room temp  usually come from plant sources  lower m.p. due to cis-arrangement (kinked shape) New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Fats are stable towards oxidation by air More convenient to handle and store New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Advantages: higher m.p.  ideal for baking turning rancid much less readily than unsaturated oils New Way Chemistry for Hong Kong A-Level 3A

Application : - hardening of plant oils Plant oil (polyunsaturated liquid with low m.p.) Partial hydrogenation Margarine (soft unsat’d solid with higher m.p.) Complete hydrogenation Animal fat (hard sat’d solid with still higher m.p.) New Way Chemistry for Hong Kong A-Level 3A

H2 / Ni 150°C, atm trans-fat  coronary heart disease New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation
Hydrogenation of vegetable oils produces margarine New Way Chemistry for Hong Kong A-Level 3A

Catalytic Hydrogenation Margarine and butter do not have sharp m.p. because they are NOT pure substances. They are mixtures containing different triesters. New Way Chemistry for Hong Kong A-Level 3A

Electrophilic Addition Reactions(AdE) Addition of electrophiles to the C=C double bond of alkenes New Way Chemistry for Hong Kong A-Level 3A

Electrophiles that attack the C=C double bond include  protons (H+)  neutral species in which the molecule is polarized, e.g. bromine New Way Chemistry for Hong Kong A-Level 3A

(a) Addition of halogens in non-aqueous solvents CH3CCl3 X = Cl, Br or I Occurs with or without light Addition is preferred to substitution Reaction mechanism is not required New Way Chemistry for Hong Kong A-Level 3A

+ Br +  bromonium ion New Way Chemistry for Hong Kong A-Level 3A

trans-addition New Way Chemistry for Hong Kong A-Level 3A

(a) Addition of halogens in non-aqueous solvents New Way Chemistry for Hong Kong A-Level 3A

(a) Addition of halogens in non-aqueous solvents e.g. New Way Chemistry for Hong Kong A-Level 3A

(a) Addition of halogens in non-aqueous solvents
The decolourization of bromine in 1,1,1-trichloroethane is a useful test for unsaturation A drop of bromine dissolved in 1,1,1-trichloroethane is added to an alkene The reddish brown colour of bromine is decolourized New Way Chemistry for Hong Kong A-Level 3A

(b) Addition of halogens in aqueous solutions -OH comes from H-OH which is in excess. Reaction mechanism is not required. New Way Chemistry for Hong Kong A-Level 3A

(b) Addition of halogens in aqueous solutions e.g. The consequent decolourization of the reddish brown colour of bromine water is also a test for unsaturation New Way Chemistry for Hong Kong A-Level 3A

+ Br +  bromonium ion New Way Chemistry for Hong Kong A-Level 3A

bromohydrin New Way Chemistry for Hong Kong A-Level 3A

Q.32 NaCl(aq) + + New Way Chemistry for Hong Kong A-Level 3A

Cl New Way Chemistry for Hong Kong A-Level 3A

Q.32 NaI(aq) + + New Way Chemistry for Hong Kong A-Level 3A

Q.32 NaNO3(aq) + + New Way Chemistry for Hong Kong A-Level 3A

NO3 New Way Chemistry for Hong Kong A-Level 3A

(c) Addition of H – X X = Br, Cl, OSO3H, OH, etc. Mechanism required Acid-catalyzed hydration New Way Chemistry for Hong Kong A-Level 3A

Addition of Hydrogen Bromide A molecule of HBr adds to the C=C double bond of an alkene Give a bromoalkane New Way Chemistry for Hong Kong A-Level 3A

Reaction Mechanism: Electrophilic Addition Reactions of Hydrogen Bromide to Alkenes
rate-determining step sp2 hybridized carbonium ion fast Br is a nucleophile New Way Chemistry for Hong Kong A-Level 3A

If the resulting C is chiral
sp2 hybridized trigonal planar racemic mixture 50% fast * If the resulting C is chiral New Way Chemistry for Hong Kong A-Level 3A

Q.33 (a) one  bond and one  bond are broken (b) two  bonds are formed (c) Heat evolved during bond formation > Heat required during bond breaking Addition reactions are usually exothermic view movie New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule
CH2=CH2 & CH3CH=CHCH3 are symmetrical alkenes. CH3CH=CH2 is an asymmetrical alkene. New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule A hydrogen halide can add to an asymmetrical alkene in either of the two ways The reaction proceeds to give a major product preferentially  the reaction is said to exhibit “regioselectivity” New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule the addition of HBr to ethene produces bromoethane as the only product New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule When but-2-ene reacts with HBr  2-bromobutane is formed as the only product New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule When propene reacts with HBr  the major product is 2-bromopropane  the minor product is 1-bromopropane New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule H is given to the rich New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule Markovnikov’s rule states that in the addition of HX to an asymmetrical alkene, the hydrogen atom adds to the carbon atom of the carbon-carbon double bond that already has the greater number of hydrogen atoms New Way Chemistry for Hong Kong A-Level 3A

Regioselectivity of Hydrogen Halide Addition: Markovnikov’s Rule The products formed according to this rule are known as Markovnikov products New Way Chemistry for Hong Kong A-Level 3A

Stability of Carbocation and Mechanistic Explanation of the Markovnikov’s Rule Carbocations are a chemical species that contains a positively charged carbon Very unstable Exist transiently during the reaction Classified as primary, secondary or tertiary  according to the number of alkyl groups that are directly attached to the positively charged carbon New Way Chemistry for Hong Kong A-Level 3A

Stability of Carbocation and Mechanistic Explanation of the Markovnikov’s Rule The more stable the carbocation  the more stable the transition state  the lower the activation energy  the faster its formation New Way Chemistry for Hong Kong A-Level 3A

Stability of Carbocation and Mechanistic Explanation of the Markovnikov’s Rule The stability of the carbocations increases in the order: New Way Chemistry for Hong Kong A-Level 3A

Alkyl groups stabilize the positively charged carbocation by positive inductive effect New Way Chemistry for Hong Kong A-Level 3A

A greater number of alkyl groups  release more electrons to the positively charged carbon  increase the stability of the carbocation New Way Chemistry for Hong Kong A-Level 3A

Stability of Carbocation and Mechanistic Explanation of the Markovnikov’s Rule Consider the addition of HBr to propene: New Way Chemistry for Hong Kong A-Level 3A

Stability of Carbocation and Mechanistic Explanation of the Markovnikov’s Rule The hydrobromination of propene involves two competing reactions: New Way Chemistry for Hong Kong A-Level 3A

Since the formation of carbocation is the rate-determining step, the overall reaction is faster if it involves the formation of a more stable carbocation. New Way Chemistry for Hong Kong A-Level 3A

Q.34(a) X = Cl, Br, or I New Way Chemistry for Hong Kong A-Level 3A

Q.34(b) +  heat cold New Way Chemistry for Hong Kong A-Level 3A

On heating, alkyl hydrogensulphates form alkenes and sulphuric acid New Way Chemistry for Hong Kong A-Level 3A

Separation of a mixture containing an alkane and an alkene.
Alkane / Alkene conc. H2SO4 / cold no reaction Alkane addition insoluble in conc. H2SO4 dissolved in conc. H2SO4 Separated by separating funnel New Way Chemistry for Hong Kong A-Level 3A

Separation of a mixture containing an alkane and an alkene. Alkane / Alkene conc. H2SO4 / cold no reaction Alkane addition insoluble in conc. H2SO4 heat Alkene dissolved in conc. H2SO4 New Way Chemistry for Hong Kong A-Level 3A

conc. H2SO4 + H2O  dilute H2SO4
Alkyl hydrogensulphates can be easily hydrolyzed to alcohols by heating with water conc. H2SO4 + H2O  dilute H2SO4 acid-catalyzed hydration New Way Chemistry for Hong Kong A-Level 3A

(c) Addition of H – X X = Br, Cl, OSO3H, OH, etc. Mechanism required Acid-catalyzed hydration New Way Chemistry for Hong Kong A-Level 3A

Acid-catalyzed hydration +  New Way Chemistry for Hong Kong A-Level 3A

Acid-catalyzed hydration The acid catalyst is regenerated + H3O+ New Way Chemistry for Hong Kong A-Level 3A

Q.34(d) 3 2 New Way Chemistry for Hong Kong A-Level 3A

Q.34(c) +  I – Cl electron-donating 3 1 EN : C = I = 2.5 New Way Chemistry for Hong Kong A-Level 3A

Q.34(e) H – Cl More destabilized by negative inductive effect New Way Chemistry for Hong Kong A-Level 3A

Q.34(f) H – Cl The resonance effect more than compensates the negative inductive effect of Cl New Way Chemistry for Hong Kong A-Level 3A

Q.34(g) H – Br > 2 1 New Way Chemistry for Hong Kong A-Level 3A

The +ve charge is shared by the benzene ring by resonance effect. Stabilized by resonance effect as well as inductive effect(2) New Way Chemistry for Hong Kong A-Level 3A

benzylic carbocation More stable than 3 carbocation New Way Chemistry for Hong Kong A-Level 3A

Q.34(h) excess H – F New Way Chemistry for Hong Kong A-Level 3A

2 1 Allylic carbocation is stabilized by resonance effect. Stabilized by resonance effect as well as inductive effect Stability : - Benzylic > allylic > 3 > 2 > 1 > CH3+ New Way Chemistry for Hong Kong A-Level 3A

H – F less destabilized by –ve I-effect of F New Way Chemistry for Hong Kong A-Level 3A

Effect of substituents on the reactivity of AdE 1. Electron-donating groups increase the reactivity by (a)  the electron density of C=C bond, thus making it more susceptible to electrophilic attack. (b) Stabilizing the carbocation intermediate/T.S. by +ve I-effect and/or resonance effect, thus lowering the Ea for the rate-determining step. New Way Chemistry for Hong Kong A-Level 3A

Effect of substituents on the reactivity of AdE 2. Resonance effect > inductive effect 3. Electron-withdrawing groups lower the reactivity by working in the opposite ways. New Way Chemistry for Hong Kong A-Level 3A

Oxidation of alkenes (a) Combustion More sooty and luminous than that of corresponding alkanes due to higher carbon contents New Way Chemistry for Hong Kong A-Level 3A

(b) Reaction with KMnO4 KMnO4, H+ or OH cold Used as a test for alkenes KMnO4, H+ or OH heat carbonyl products New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH heat If all R groups are alkyl groups, ketones will be the final products. KMnO4, H+ or OH heat New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH heat No reaction New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH heat If either R1 or R2 is H / either R3 or R4 is H, further oxidation of aldehydes to carboxylic acid will occur. KMnO4, H+ or OH heat New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH heat aldehyde carboxylic acid New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH heat If both R1 & R2 are H / both R3 & R4 are H, further oxidation to first methanoic acid and then CO2 will occur. KMnO4, H+ or OH heat New Way Chemistry for Hong Kong A-Level 3A

KMnO4, H+ or OH 2CO H2O heat methanoic acid New Way Chemistry for Hong Kong A-Level 3A

(c) Ozonolysis Further oxidation of aldehyde to carboxylic acid by H2O2 is inhibited using Zn dust and CH3COOH New Way Chemistry for Hong Kong A-Level 3A

(c) Ozonolysis 1. O3 2. Zn dust / H2O 1. O3 2. Zn dust / H2O New Way Chemistry for Hong Kong A-Level 3A

Oxidative cleavage can be used to locate C=C bond in an unknown sample New Way Chemistry for Hong Kong A-Level 3A

Q.36 (3Z)-2-methylpenta-1,3-diene (3E)-2-methylpenta-1,3-diene New Way Chemistry for Hong Kong A-Level 3A

Q.36 (3E)-3-methylpenta-1,3-diene (3Z)-3-methylpenta-1,3-diene New Way Chemistry for Hong Kong A-Level 3A

The END New Way Chemistry for Hong Kong A-Level 3A

28.4 Preparation of Alkenes (SB p.173) Example 28-4 Classify the following alcohols as primary, secondary or tertiary alcohols. (a) CH3CHOHCH2CH3 (b) CH3CH2CH2OH (c) (CH3)2COHCH2CH2CH3 Answer (a) It is a secondary alcohol. (b) It is a primary alcohol. (c) It is a tertiary alcohol. Back New Way Chemistry for Hong Kong A-Level 3A

28.4 Preparation of Alkenes (SB p.173) Back Check Point 28-4 Classify the following haloalkanes as primary, secondary or tertiary haloalkanes. (a) (c) (b) (a) A secondary haloalkane (b) A primary haloalkane (c) A tertiary haloalkane Answer New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.177) Check Point 28-5A Of the isomeric C5H11+ carbocations, which one is the most stable? Answer The more stable C5H11+ carbocation is the tertiary carbocation as shown below: Back New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.179)
Back Let's Think 1 Both alkanes and alkenes undergo halogenation. The halogenation of alkanes is a free radical substitution reaction while the reaction of alkenes with halogens is an electrophilic addition reaction. Can you tell two differences between the products formed by the two different types of halogenation? Answer Alkenes give dihalogenated products while alkanes usually give polysubstituted products. Another difference is the position of the attachment of the halogen atom. For alkenes, the halogen atom is fixed to the carbon atom of the carbon=carbon double bond. In the substitution reaction of alkanes, the position of the halogen atom varies. New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.183) Check Point 28-5B (a) What chemical tests would you use to distinguish between two unlabelled bottles containing hexane and hex-1-ene respectively? Answer (a) We can perform either one of the following tests: Hex-1-ene can decolourize bromine water or chlorine water in the dark while hexane cannot. Hex-1-ene can decolourize acidified potassium manganate(VII) solution while hexane cannot. New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.183) Check Point 28-5B What is the major product of each of the following reactions? (i) (ii) Answer New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.183) Check Point 28-5B (i) (ii) New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.183) Check Point 28-5B (c) Give the products for the following reactions: (i) CH3CH = CH2 + H2  (ii) CH3CH = CHCH3  (iii) CH3CH = CHCH3 + Br2  Ni conc. H2SO4 Answer New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.183) Check Point 28-5B Back (c) (i) CH3CH2CH3 (ii) (iii) New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.184) Check Point 28-5C Arrange the following carbocations in increasing order of stability. Explain your answer briefly. Answer New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.184) Check Point 28-5C The increasing order of the stability of carbocations is: Tertiary carbocations are the most stable because the three alkyl groups release electrons to the positive carbon atom and thereby disperse its charge. Primary carbocations are the least stable as there is only one alkyl group releasing electrons to the positive carbon atom. New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.184) Check Point 28-5C (b) Based on your answer in (a), arrange the following molecules in the order of increasing rates of reaction with hydrogen chloride. Answer New Way Chemistry for Hong Kong A-Level 3A

28.5 Reactions of Alkenes (SB p.184) Check Point 28-5C Back (b) The reaction of these compounds with hydrogen chloride involves the formation of carbocations. Therefore, the order of reaction rates follows the order of the ease of the formation of carbocations, i.e. the stability of carbocations: Therefore, the rates of reactions of the three compounds with hydrogen chloride increase in the order: New Way Chemistry for Hong Kong A-Level 3A

Electrophilic Addition

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