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A-level Chem > Organic synthesis part 1 > Flashcards

Organic synthesis part 1 Flashcards

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1
Q

Why is carbon-carbon bond formation important in organic synthesis? (2 points).

A
  1. Important within industry.
  2. Manufacture of medicines.
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2
Q

What are the two ways new carbon-carbon bonds are formed?

A
  1. Formation of substituted aromatic C-C.
  2. Formation of C-CN.
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3
Q

What are the reagents and conditions for alkylation of benzene? (2 points).

A
  1. Haloalkane.
  2. A halogen carrier as a catalyst.
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4
Q

Write the equation for the formation of the electrophile: CH3CH2+, using CH3CH2Br and AlBr3.

A

CH3CH2Br + AlBr3 …. CH3CH2+ + AlBr4-

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5
Q

*Write the overall reaction for the alkylation of benzene with CH3CH2Br.

A

*Refer to notes.

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6
Q

Name the mechanism for the alkylation of benzene.

A

Electrophilic substitution.

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7
Q

*Describe the mechanism of alkylation for benzene with CH3CH2+ acting as the electrophile. Write the equation for the formation of the catalyst.

A

*Refer to notes.

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8
Q

What are the reagents and conditions for the acylation of benzene? (2 points).

A
  1. Acyl chloride.
  2. Halogen carrier as a catalyst.
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9
Q

*Write the overall reaction between benzene and CH3COCl.

A

*Refer to notes.

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10
Q

Name the mechanism for the acylation of benzene.

A

Electrophilic substitution.

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11
Q

*Describe the mechanism for the acylation of benzene with CH3COCl. Write the equation for the regeneration of the catalyst used.

A

*Refer to notes.

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12
Q

What are the reagents for the reaction between carbonyl compounds and HCN? (2 points).

A
  1. NaCN
  2. H2SO4
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13
Q

What type of reaction is carbonyl compounds reacting with HCN?

A

Nucleophilic addition.

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14
Q

*Write an equation for the reaction between butanal and HCN.

A

*Refer to notes.

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15
Q

*Describe the mechanism for the reaction between propanone with HCN. Name the product.

A

*Refer to notes.

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16
Q

Why is HCN made in situ? (2 points).

A
  1. HCN is an extremely poisonous volatile liquid.
  2. If made in situ, safety is improved and reaction rate increases.
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17
Q

Name the type of reaction that happens when haloalkanes react with NaCN (in ethanol)?

A

Nucleophilic substitution.

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18
Q

*Write the equation for the reaction between 1-chloropropane with NaCN.

A

*Refer to notes.

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19
Q

*Describe the mechanism for the reaction between 1-chloropropane and NaCN.

A

*Refer to notes.

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20
Q

What are the reagents and conditions for the reduction of a nitrile to form an amine? (2 points).

A
  1. H2(g)
  2. Ni catalyst.
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21
Q

What type of reaction is the reduction of a nitrile to an amine?

A

Addition.

22
Q

*Write the equation for the reaction of butanenitrile with H2(g).

A

*Refer to notes.

23
Q

What does the reduction of a nitrile form?

A

An amine- NH2.

24
Q

What does the hydrolysis of a nitrile form?

A

A carboxylic acid- COOH.

25
Q

What are the reagents and conditions for the hydrolysis of a nitrile into a carboxylic acid? (2 points).

A
  1. HCl(aq)
  2. Reflux
26
Q

*Write the equation for the hydrolysis of ethanenitrile into ethanoic acid.

A

*Refer to notes.

27
Q

*Write the equation for the hydrolysis of hydroxypropane nitrile.

A

*Refer to notes.

28
Q

*What is the functional group of an ester?

A

*Refer to notes.

29
Q

What are the three different methods for preparing esters?

A
  1. Carboxylic acid
  2. Acid anhydride
  3. Acyl chloride
30
Q

Identify 1 feature that is different in each preparation of esters compared to the other two types. (3 points).

A
  1. Carboxylic acid prep is a reversible reaction so gives a low yield. It also requires a catalyst and heat.
  2. Acid anhydride preparation produces a carboxylic acid as a by-product.
  3. Acyl chloride preparation produces a molecule of HCl as a by-product.
31
Q

*What is the functional group of an amide?

A

*Refer to notes.

32
Q

Give two ways amides can be formed by the reaction of amines (-NH2), or ammonia (NH3) with…

A
  1. Acyl chloride.
  2. Carboxylic acid.
33
Q

*Draw what a primary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).

A

*Refer to notes.

34
Q

*Draw what a secondary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).

A

*Refer to notes.

35
Q

*Draw what a tertiary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).

A

*Refer to notes.

36
Q

What are the reagents for the formation of primary amides? (2 points).

A
  1. NH3
  2. Acyl chloride.
37
Q

What are the conditions for the formation of primary amides?

A

Room temperature

38
Q

*Write an equation for the formation of a primary amide, using ethanoyl chloride and ammonia. Name the products.

A

*Refer to notes.
Primary amide: ethane amide.
Ammonium chloride.

39
Q

What are the reagents for the formation of secondary amides? (2 points).

A
  1. Primary amine.
  2. Acyl chloride.
40
Q

What are the conditions for the formation of secndary amides?

A

Room temperature.

41
Q

*Write the equation for the formation of a secondary amide using ethanoyl chloride and methylamine. Name the products.

A

*Refer to notes.
Secondary amide- N-methylethanamide.
Methylammonium chloride.

42
Q

What are the reagents and conditions of the acid hydrolysis of esters? (2 points).

A
  1. HCl(aq)
  2. Reflux
43
Q

*Write a balanced equation for the acid hydrolysis of methyl propanoate.

A

*Refer to notes.

44
Q

What are the reagents and conditions used for the acid hydrolysis of amides? (2 points).

A
  1. HCl(aq)
  2. Reflux.
45
Q

*Write the equation for the acid hydrolysis of N-methylethanamide. Name the products.

A

*Refer to notes.
Ethanoic acid.
Methylammonium chloride.

46
Q

What are the reagents and conditions ofr the alkaline hydrolysis of of esters? (2 points)

A
  1. NaOH(aq)
  2. Reflux.
47
Q

*Write an equation for the reaction of alkaline hydrolysis of ethyl methanoate.

A

*Refer to notes.

48
Q

In the alkaline hydrolysis of an amide, which of the products is changed by the alkali present?

A

The carboxylic acid formed loses a H+ forming a salt.

49
Q

What are the reagents and conditions for the alkaline hydrolysis of an amide? (2 points)

A
  1. NaOH(aq).
  2. Reflux.
50
Q

*Write an equation for the alkaline hydrolysis of N-methylethanamide, CH3CONHCH3. Name the products.

A

*Refer to notes.
Sodium ethanoate.
Methylamine.

A-level Chem (30 decks)

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