Organic Chemistry 2.0 - (most of) Synthesis

Question 1

When naming a molecule, when do you not include numbers to indicate the position of a branch or functional group?

Answer 1

when there is only one place it can be

Question 2

What do you call a carboxylic acid, with a body of 3 carbons and a 1 carbon chain on the second carbon?
1. Butanoic aicd
2. 2-methylpropanoic acid
3. methypropanoic aicd

Answer 2

1. no
2. technically yes, but also no, because answering this shows that you don’t know why the number is important (there is no other place the methyl branch could be)
3. yes

Question 3

When a chemical bond is broken, the shared electrons can be redistributed in which two ways?

Answer 3

Heterolytically and homolytically

Question 4

What are the products of homolytic and heterolytic reactions?

Answer 4

homo: two neutral radicals
hetero: two oppositely charged ions

Question 5

Curly arrows represent…
Difference between full and half head arrow…
Bond breaking is represented by…
Bond forming is represented by…

Answer 5

the movement of electrons.
a pair of electrons Vs one electron
arrow(s) pointing from the bond to the atom(s)
arrow(s) pointing in between two atoms

Question 6

What are carbocations?
What is a nucleophile?
What is an electrophile?

Answer 6

1. positive carbon atoms/
2. something attracted to nucleus/+ve/ electron deficient stuff. - is itself -ve/electron rich
3. something attracted to electrons/-ve/electron rich areas - is itself +ve/electron deficient.
   (electron rich areas include the O in H2O and the N in NH3)

Question 7

Name 5 nucleophiles.
Name 5 electrophiles.

Answer 7

OH-, NH3, OH2, CN-, Halogen ions
H+, NO2+, SO3+, BF3, AlCl3

Question 8

All manner of things can be classified as primary, secondary or tertiary, based on…

Answer 8

the number of hydrogens attached to the carbon with the thingy on it (halogen in monohaloalkane, hydroxyl in alcohols, - or no of hydrogens on the N in amines)

Question 9

Monohaloalkanes can undergo two types of reaction.
What are they?

Answer 9

elimination.
Nucleophilic substitution

Question 10

Elimination of a monohaloalkane.
- what are the conditions?
- what is the product?

Answer 10

heat under reflux with Ethanoic Sodium or Potassium Hydroxide.
an alkene :)

Question 11

Nucleophilic substitution of a monohaloalkane.
- name the products for all of the variants of this reaction type.
- state the conditions for each.

Answer 11

1. nitrile - Ethanolic Na/K cyanide
2. alcohol - aqueous Na/K OH
3. ether - alcoholic alkoxides
   all heat under reflux

Question 12

When forming an ether from a monohaloalkane, the alkoxide must be the same ___ ___ as the ___ it’s dissolved in.

Answer 12

chain length, alcohol

Question 13

Alcohols react to form which 4 things?
State the reaction type and conditions for each.

Answer 13

1. Aldehyde/ketone - oxidation reaction - requires acidified permanganate/hot copper(II) oxide
2. Alkene - elimination reaction - heat under reflux with Ethanolic Na/K OH - requires conc. Sulfuric acid
3. Alkoxides - REDOX reaction - reacts with reactive metals (Na/K)
4. ester - condensation esterification - reacts with carboxylic acid (requires conc. Sulfuric acid) or acid chloride

Question 14

How are acid chlorides formed?

Answer 14

carboxylic acid reacts with phosphorus pentachloride (PCl5)

Question 15

What are the four reactions of alkenes?
State the reactants, products and conditions required for each.
All of these reactions are of which type?

Answer 15

1. Hydration. alkene + water = alcohol [requires acid catalyst]
2. Hydrogenation. alkene + hydrogen = alkane [requires catalyst (Ni/Pt - not required knowledge)]
3. Hydrohalogenation. alkene + hydrogen halide = monohaloalkane
4. Halogenation. alkene + halogen = dihaloalkane.

Electrophilic addition

Question 16

Carboxylic acids can be formed in four different ways.
Name each of them and provide the conditions.

Answer 16

1. Hydrolysis of an ester
2. hydrolysis of a nitrile
3. hydrolysis of an amide [all hydrolysis reactions require heat under reflux with aqueous acid]
4. oxidation of an aldehyde [hot copper(II) oxide

Question 17

Carboxylic acids can take place in six different reactions. Name each reaction and state the products formed and reactants required.

Answer 17

1. alkali - forms salt
2. Metal - forms salt
3. carbonate - forms salt
4. alcohol - forms ester [esterification]
5. amine - forms alkyamonium salt which forms amide when heated
6. LiAlH4 + ethoxyethane - forms aldehyde [reduction]

Question 18

Amines react with two thingies to form some stuff. Provide the names of the aforementioned stuff and things.

Answer 18

1. carboxylic acid [to form an alkyamonium salt, which must be heated to form an amide (or not if ur an alkyamonium salt enthusiast)]
2. mineral acid [to form a salt]

Question 19

Finaly, what are the four reactions of benzene?
What are the reactants, products, reaction type and conditions??

Answer 19

1. benzene + monohaloalkane = alkylbenzene [alkylation reaction - the conditions require AlCl3 as a catalyzer]
2. benzene + chlorine/bromine = chloro/bromobenzene [chlorination or bromination reaction - (halogenation) - requires FeCl2 or FeBr3 as a catalyst]
3. benzene + NO2+ = nitrobenzene [requires concentrated sulfuric and nitric acid]
4. benzene + HOSO2+ = benzenesulfonic aicd [requires concentrated sulfuric acid]