RX: Reactions

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Last updated 12:45 PM on 6/12/26
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12 Terms

1
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Nucleophilic substitution with OH- to form alcohol

RnC: dilute NaOH, heat

<p>RnC: dilute NaOH, heat</p>
2
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Nucleophilic substitution with CN- to form nitriles

RnCs: KCN in ethanol, heat OR ethanolic KCN, heat

AKA step-up reaction as carbon chain increases by 1 C atom

<p>RnCs: KCN in ethanol, heat OR ethanolic KCN, heat</p><p>AKA step-up reaction as carbon chain increases by 1 C atom</p>
3
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acidic hydrolysis of nitriles

RnCs: dilute H2SO4, heat

<p>RnCs: dilute H<sub>2</sub>SO<sub>4</sub>, heat</p>
4
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alkaline hydrolysis of nitriles

RnCs: dilute NaOH, heat

<p>RnCs: dilute NaOH, heat</p>
5
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nucleophilic substitution with ammonia to form amines

RnCs: NH3 in ethanol, heated under high pressure

  • ethanol is solvent for ammonia

  • as amines can readily react with halogenoalkane, further reactions can occur to form more subsituted amines (pri, sec, ter, qua)

<p>RnCs: NH3 in ethanol, heated under high pressure</p><ul><li><p>ethanol is solvent for ammonia</p></li><li><p>as amines can readily react with halogenoalkane, further reactions can occur to form more subsituted amines (pri, sec, ter, qua)</p></li></ul><p></p>
6
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Elimination

RnCs: NaOH in ethanol, heat

<p>RnCs: NaOH in ethanol, heat</p>
7
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Why are halogenoarenes less susceptible to nucleophilic substitution than halogenoalkanes?

bond strength of C-X bond

  • lone pair of e- on halogen atom delocalises into the benzene ring, resulting in partial double bond character in C-X bond

  • making bond length shorter and bond strength stronger

  • C-X bond becomes more difficult to break

Steric hinderance

  • rear side of C-X bond is blocked by bulky benzene ring, giving steric hinderance to nucleophilic attack

repellence

  • the pi-electron cloudof benzene ring repels lone pair of e- of incoming nucleophile

8
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describe reactivity of halogenoarenes in electrophilic subsitution

  • reactive but less susceptible due deactivation by halogen substituent (T >50 for nitration)

  • halogen substituent is 2,4-directing

9
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describe steps for distinguishing test for halogenoalkanes

  1. add excess NaOH(aq) and heat (release X- ions)

  2. add excess dilute HNO3 (remove unreacted OH- so brown AgO ppt won’t be formed)

  3. Add AgNo3(aq) and observe ppt formed

  4. decant and wash ppt in DI water, then add NH3(aq) to check for solubility (colours of AgCl and AgBr are difficult to differentiate)

10
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Observations for chloroalkane, RCl

  • white ppt (formed in a longer time than RBr)

  • dissolves in dilute NH3(aq)

11
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Observations for bromoalkane, RBr

  • cream ppt (formed in longer time than RI)

  • dissolves in concentrated NH3

12
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Observations for iodoalkane, RI

  • yellow ppt (formed almost immediately)

  • insoluble in even concentrated NH3