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A-level Chem > Organic synthesis part 1 > Flashcards

Organic synthesis part 1 Flashcards

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?

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
What are the reagents and conditions for the hydrolysis of a nitrile into a carboxylic acid? (2 points).
1. HCl(aq) 2. Reflux
26
*Write the equation for the hydrolysis of ethanenitrile into ethanoic acid.
*Refer to notes.
27
*Write the equation for the hydrolysis of hydroxypropane nitrile.
*Refer to notes.
28
*What is the functional group of an ester?
*Refer to notes.
29
What are the three different methods for preparing esters?
1. Carboxylic acid 2. Acid anhydride 3. Acyl chloride
30
Identify 1 feature that is different in each preparation of esters compared to the other two types. (3 points).
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
*What is the functional group of an amide?
*Refer to notes.
32
Give two ways amides can be formed by the reaction of amines (-NH2), or ammonia (NH3) with...
1. Acyl chloride. 2. Carboxylic acid.
33
*Draw what a primary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
34
*Draw what a secondary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
35
*Draw what a tertiary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
36
What are the reagents for the formation of primary amides? (2 points).
1. NH3 2. Acyl chloride.
37
What are the conditions for the formation of primary amides?
Room temperature
38
*Write an equation for the formation of a primary amide, using ethanoyl chloride and ammonia. Name the products.
*Refer to notes. Primary amide: ethane amide. Ammonium chloride.
39
What are the reagents for the formation of secondary amides? (2 points).
1. Primary amine. 2. Acyl chloride.
40
What are the conditions for the formation of secndary amides?
Room temperature.
41
*Write the equation for the formation of a secondary amide using ethanoyl chloride and methylamine. Name the products.
*Refer to notes. Secondary amide- N-methylethanamide. Methylammonium chloride.
42
What are the reagents and conditions of the acid hydrolysis of esters? (2 points).
1. HCl(aq) 2. Reflux
43
*Write a balanced equation for the acid hydrolysis of methyl propanoate.
*Refer to notes.
44
What are the reagents and conditions used for the acid hydrolysis of amides? (2 points).
1. HCl(aq) 2. Reflux.
45
*Write the equation for the acid hydrolysis of N-methylethanamide. Name the products.
*Refer to notes. Ethanoic acid. Methylammonium chloride.
46
What are the reagents and conditions ofr the alkaline hydrolysis of of esters? (2 points)
1. NaOH(aq) 2. Reflux.
47
*Write an equation for the reaction of alkaline hydrolysis of ethyl methanoate.
*Refer to notes.
48
In the alkaline hydrolysis of an amide, which of the products is changed by the alkali present?
The carboxylic acid formed loses a H+ forming a salt.
49
What are the reagents and conditions for the alkaline hydrolysis of an amide? (2 points)
1. NaOH(aq). 2. Reflux.
50
*Write an equation for the alkaline hydrolysis of N-methylethanamide, CH3CONHCH3. Name the products.
*Refer to notes. Sodium ethanoate. Methylamine.

A-level Chem (30 decks)

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