Organic Reactions Flashcards

1
Q

Ethanoyl Chloride + water

Describe the reaction and give the products

A

Ethanoic acid + HCl

Vigorous

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2
Q

Acyl chloride + alcohol

Give the products and describe the reaction

A

Ester + HCl

Goes to completion unlike COOH + OH

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3
Q

Propanoyl chloride + conc. ammonia solution

Give the products and describe the reaction

A

Propanamide + HCl

Room temperature, violent

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4
Q

How would you form a chloroalkane from an alcohol?

A

PCl5

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5
Q

Reaction of acyl chloride + amine

A

N-substituted amide + HCl

Violent reaction

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6
Q

Amine + acid —>

A

Ammonium salt

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7
Q

CH3CH2NH2 + HCl –>

A

CH3CH2NH3+Cl- (salt)

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8
Q

How would you form a secondary amine?

A

Primary amine + halogenoalkane

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9
Q

Ethanoyl chloride + phenylamine –>

A

Two reactions:

N-phenylethanamide + HCl

then:

Phenylamine + HCl –> Phenylammonium chloride

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10
Q

Equation for the combustion of ethanol

A

C2H5OH + 3O2 –> 2CO2 + 3H2O

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11
Q

Why does the reaction between PCl5 and an alcohol not need heating?

A

The reaction is very vigorous at room temperature

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12
Q

What are the two inorganic products formed from the reaction of PCl5 and an alcohol?

A

Phosphorus oxychloride (POCl3) and Hydrogen chloride (HCl)

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13
Q

Give the equation for the reaction between PCl5 and propan-1-ol

A

CH3CH2CH2OH + PCl5 –> CH3CH2CH2Cl +

                                                    POCl3 + HCl
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14
Q

How would you chlorinate a tertiary alcohol?

A

Add conc. HCl at room temperature, shake

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15
Q

How would you brominate an alcohol?

A

Warm with a mixture of potassium bromide and 50% concentrated sulfuric acid

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16
Q

Give the three equations for the bromination of butan-1-ol

A

KBr + H2SO4 –> KHSO4 + HBr

2KBr + H2SO4 –> K2SO4 + 2HBr

CH3CH2CH2CH2OH + HBr –>

                                      CH3CH2CH2CH2Br +H2O
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17
Q

Write the equation for the formation of the reactant that reacts with an alcohol to form an iodoalkane

A

2P + 3I2 –> 2PI3

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18
Q

What would you use in the iodination of an alcohol?

A

A mixture of red phosphorus and iodine, heat under reflux

19
Q

Give the equation for the reaction between ethanol and phosphorus(III) iodide

A

3C2H5OH + PCl3 –> 3C2H5I + H3PO3

20
Q

What is H3PO3?

A

Phosphonic acid (or phosphorous acid)

21
Q

What is formed in the dehydration of an alcohol?

A

An alkene

22
Q

What is the inorganic product of a dehydration reaction of an alcohol?

A

H2O

23
Q

What do you react alcohols with to dehydrate them?

A

Conc. phosphoric acid

24
Q

What are the two possible products of the dehydration of butan-1-ol?

A

But-1-ene and But-2-ene

25
Q

When butan-2-ol is dehydrated, there is more than one organic product. Explain why there is only one pair of E/Z isomers when pentan-3-ol is dehydrated

A

It is symmetrical so the double bond can only form between the second and third carbon whereas in butan-2-ol the double bond could form between the first and second carbon or the second and third carbon

26
Q

What type of solution do small amines form when dissolved in water?

A

An alkaline solution

-the amine takes a H+ ion from water forming alkyl ammonium ions and OH- ions

27
Q

RCOOH + PCl5 –>

A

RCOCl + POCl3 + HCl

28
Q

RCOOH —-> RCH2OH

A

LiAlH4 in dry ether

29
Q

CH3COOH + NaOH –>

A

CH3COONa + H2O

30
Q

2CH3COOH + Na2CO3 —>

How could you test for a reaction?

A

2CH3COONa + H2O + CO2

Use limewater

31
Q

CH3COOH + NaHCO3 –>

A

CH3COONa + H2O + CO2

32
Q

Are carboxylic acids soluble in water?

A
  • Shorter chained ones are as they are very polar and form hydrogen bonds with the water molecules
  • solubility decreases as the length of the chain increases as they have stronger intermolecular forces between
  • if these stronger intermolecular forces are stronger than hydrogen bonding with water would be then the carboxylic acid won’t dissolve
33
Q

a) Explain why propanoic acid behaves as an acid but propanol does not
b) Describe a simple test to distinguish between propanol and propanoic acid

A

a) Propanoic acid partially dissociates in water to release H+ ions. Propanol doesn’t
b) Add sodium carbonate. Propanoic acid will cause fizzing of bubbles of CO2. Propanol will show no reaction

34
Q

What is needed in the reaction of a carboxylic acid and an alcohol?

What is formed?

A

Heat, acid catalyst

An ester

35
Q

How would you retrieve the ester formed from the reaction between a carboxylic acid and an alcohol?

Why would you have to do it this way?

A
  • The reaction is reversible
  • Product must be separated as it forms
  • Use distillation as the apparatus for the reaction
  • Add sodium carbonate to react with any acid still present in the mixture
  • The ester will form on top of the aqueous layer and can be separated using a separating funnel
36
Q

What type of reaction is the reaction between amine and ethanoyl chloride?

A

Addition-elimination

-Two molecules join together, a small molecule is then eliminated

37
Q

Amine + halogenoalkane –>

A

Secondary amine + hydrogen halide

38
Q

CH3CH2CH2CH2NH2 + CH3CH2Cl –>

A

CH3CH2CH2CH2NHCH2CH3 + HCl

39
Q

What are the problems of reacting an amine with a halogenoalkane?

A

Forms a secondary amine that then can react with more halogenoalkane to produce a tertiary amine which will then react to form a quaternary salt

40
Q

What is the solubility of amines like?

A

Very soluble but solubility decreases as the chain length increases

Form hydrogen bonds with the water

41
Q

Functional group of an amide

A

RCONH2

42
Q

Why would there be two reactions when an acyl chloride is reacted with conc. aqueous ammonia?

A

CH3CH2COCl + NH3 –> CH3CH2CONH2 + HCl

NH3 will react with HCl to form NH4Cl

43
Q

How would you form a primary amine from a nitrile?

A

Use LiAlH4 in dry ether

CH3CN + 4[H] –> CH3CH2NH2