Organic synthesis part 1 Flashcards
Why is carbon-carbon bond formation important in organic synthesis? (2 points).
- Important within industry.
- Manufacture of medicines.
What are the two ways new carbon-carbon bonds are formed?
- Formation of substituted aromatic C-C.
- Formation of C-CN.
What are the reagents and conditions for alkylation of benzene? (2 points).
- Haloalkane.
- A halogen carrier as a catalyst.
Write the equation for the formation of the electrophile: CH3CH2+, using CH3CH2Br and AlBr3.
CH3CH2Br + AlBr3 …. CH3CH2+ + AlBr4-
*Write the overall reaction for the alkylation of benzene with CH3CH2Br.
*Refer to notes.
Name the mechanism for the alkylation of benzene.
Electrophilic substitution.
*Describe the mechanism of alkylation for benzene with CH3CH2+ acting as the electrophile. Write the equation for the formation of the catalyst.
*Refer to notes.
What are the reagents and conditions for the acylation of benzene? (2 points).
- Acyl chloride.
- Halogen carrier as a catalyst.
*Write the overall reaction between benzene and CH3COCl.
*Refer to notes.
Name the mechanism for the acylation of benzene.
Electrophilic substitution.
*Describe the mechanism for the acylation of benzene with CH3COCl. Write the equation for the regeneration of the catalyst used.
*Refer to notes.
What are the reagents for the reaction between carbonyl compounds and HCN? (2 points).
- NaCN
- H2SO4
What type of reaction is carbonyl compounds reacting with HCN?
Nucleophilic addition.
*Write an equation for the reaction between butanal and HCN.
*Refer to notes.
*Describe the mechanism for the reaction between propanone with HCN. Name the product.
*Refer to notes.
Why is HCN made in situ? (2 points).
- HCN is an extremely poisonous volatile liquid.
- If made in situ, safety is improved and reaction rate increases.
Name the type of reaction that happens when haloalkanes react with NaCN (in ethanol)?
Nucleophilic substitution.
*Write the equation for the reaction between 1-chloropropane with NaCN.
*Refer to notes.
*Describe the mechanism for the reaction between 1-chloropropane and NaCN.
*Refer to notes.
What are the reagents and conditions for the reduction of a nitrile to form an amine? (2 points).
- H2(g)
- Ni catalyst.
What type of reaction is the reduction of a nitrile to an amine?
Addition.
*Write the equation for the reaction of butanenitrile with H2(g).
*Refer to notes.
What does the reduction of a nitrile form?
An amine- NH2.
What does the hydrolysis of a nitrile form?
A carboxylic acid- COOH.
What are the reagents and conditions for the hydrolysis of a nitrile into a carboxylic acid? (2 points).
- HCl(aq)
- Reflux
*Write the equation for the hydrolysis of ethanenitrile into ethanoic acid.
*Refer to notes.
*Write the equation for the hydrolysis of hydroxypropane nitrile.
*Refer to notes.
*What is the functional group of an ester?
*Refer to notes.
What are the three different methods for preparing esters?
- Carboxylic acid
- Acid anhydride
- Acyl chloride
Identify 1 feature that is different in each preparation of esters compared to the other two types. (3 points).
- Carboxylic acid prep is a reversible reaction so gives a low yield. It also requires a catalyst and heat.
- Acid anhydride preparation produces a carboxylic acid as a by-product.
- Acyl chloride preparation produces a molecule of HCl as a by-product.
*What is the functional group of an amide?
*Refer to notes.
Give two ways amides can be formed by the reaction of amines (-NH2), or ammonia (NH3) with…
- Acyl chloride.
- Carboxylic acid.
*Draw what a primary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
*Draw what a secondary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
*Draw what a tertiary amide looks like using displayed formula (focus on the actual functional group, rather than the whole molecule).
*Refer to notes.
What are the reagents for the formation of primary amides? (2 points).
- NH3
- Acyl chloride.
What are the conditions for the formation of primary amides?
Room temperature
*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.
What are the reagents for the formation of secondary amides? (2 points).
- Primary amine.
- Acyl chloride.
What are the conditions for the formation of secndary amides?
Room temperature.
*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.
What are the reagents and conditions of the acid hydrolysis of esters? (2 points).
- HCl(aq)
- Reflux
*Write a balanced equation for the acid hydrolysis of methyl propanoate.
*Refer to notes.
What are the reagents and conditions used for the acid hydrolysis of amides? (2 points).
- HCl(aq)
- Reflux.
*Write the equation for the acid hydrolysis of N-methylethanamide. Name the products.
*Refer to notes.
Ethanoic acid.
Methylammonium chloride.
What are the reagents and conditions ofr the alkaline hydrolysis of of esters? (2 points)
- NaOH(aq)
- Reflux.
*Write an equation for the reaction of alkaline hydrolysis of ethyl methanoate.
*Refer to notes.
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.
What are the reagents and conditions for the alkaline hydrolysis of an amide? (2 points)
- NaOH(aq).
- Reflux.
*Write an equation for the alkaline hydrolysis of N-methylethanamide, CH3CONHCH3. Name the products.
*Refer to notes.
Sodium ethanoate.
Methylamine.
