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chemistry > 16 - halogenoalkanes > Flashcards

16 - halogenoalkanes Flashcards

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1
Q

reactions from which halogenoalkanes are formed

A

. free-radical substitution of alkanesc by chlorine/bromine (UV light)
. electrophilic addition of an alkene and halogen/ hydrogen halide (rtp)
. alcohol substitution (+ HX, PCl3 and heat, PCl5 at rtp, or SOCl2

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2
Q

types of halogenoalkenes

A

. primary
. secondary
. tertiary

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3
Q

halogenoalkane general formula

A

CnH2n+1X

C has partial positive charge
X has partial negative charge

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4
Q

nucleophilic substitution

A

the mechanism of the organic reaction in which a nucleophile attacks a carbon atom carrying a partial positive charge. This results in the replacement of an atom carrying a partial negative charge by the nucleophile

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5
Q

halogenoalkane hydrolysis

A

. carried out under reflux in lab
. allows heating without VOCs evaporating
. condenser, antibumping granules

CH3CH2Br H20 => CH3CH2OH + H+ + Br-

. OH more effective nucleophile than H2O
. hydrolysis slower

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6
Q

halide ion test

A

adding silver nitrate solution

. Cl - white
. Br - cream
. I - yellow

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7
Q

iodoalkane to flouroalkanes

A

fast to slow nucleophilic substitution reaction, most to least reactivr

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8
Q

C - F

A

strongest bond

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9
Q

CN- (cyanide) ions

A

CH3CH2Br + KCN => CH3CH2CN + KBr

propanenitrile formed

. KCN in ethanol
. heat under reflux

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10
Q

NH3 substitution in ethanol

A

CH3CH2Br + NH3 => CH3CH2NH + HBr

ethylamine formed

. NH3 in excess
. heat
. high pressure

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11
Q

Sn2 mechanism

A

the steps in a nucleophilic substitution reaction in which the rate of the reaction involves two reacting species

eg. hydrolysis of primary halogenoalkane

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12
Q

Sn1 mechanism

A

the steps in a nucleophilic substitution reaction in which the rate of the reaction involves only the organic reactant

eg. hydrolysis of a tertiary halogenoalkane

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13
Q

tertiary carbocation more stable than primary carbocations

A

. alkyl groups release electrons
. less charge density with less electrons
. more stable

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14
Q

secondary halogenoalkanes

A

both Sn1 and Sn2

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15
Q

halogenoalkane elimination reactions

A

reagent = ethanolic sodium hydroxide, heated

CH3CH2Br + NaOH (ethanol) => CH2CH2 + H2O + NaBr

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16
Q

halogenoalkane + NaOH (ethanol)

A

elimination reaction
alkene product

17
Q

halogenoalkane + NaOH (aq)

A

nucleophilic substitution reaction
alcohol produced

chemistry (18 decks)

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