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CheMYSTERY > Organic reactions > Flashcards

Organic reactions Flashcards

1
Q

Reflux

A

Refluxing. Many organic chemical reactions take a very long time to complete, and in order to speed up these reactions, heat is applied. However, organic compounds usually have low boiling points and are volatile, and if heated they will evaporate and be lost.
The condenser is always completely filled with water to ensure efficient cooling. The vapours, which are given off from the liquid reaction mixture, change from gas phase back to liquid phase due to heat loss. This then causes the liquid mixture to fall back into the round bottom flask. In this way, we can ensure that the chemical reaction involving organic compounds will give a higher yield of product

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2
Q

Distillation

A

Distillation is used to separate (purify) the product from any remaining reactants. It works because all the organic molecules will have different boiling points. The condenser is always completely filled with water to ensure efficient cooling.

E.g. The ester or haloalkane has a different b.pt. to other substances in the impure mixture. The liquid with the lower b.pt. will start to boil at the lower temperature, evaporate and move down the condenser, where it is cooled and returns to the liquid state.

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3
Q

Fehling’s solution

A

Fehling’s solution contains Cu2+ ions. The ions are prevented from precipitating as they are in the form of a complex ion (same observations as Benedicts with a blue solution forming a brick red precipitate as a result of oxidation.) Ketones have no reaction and the solution remains blue. Aldehydes have a reaction, the blue solution forms a brick red precipitate.

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4
Q

Addition

A

Atoms or groups of atoms are introduced into an unsaturated molecule. The molecule will become less unsaturated or saturated.

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5
Q

Elimination

A

New multiple bonds are made between carbon atoms, with the removal of a small molecule such as H2O or HCl

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6
Q

Substitution

A

Single bonds are broken and made at a carbon atom during a reaction. An atom, or group of atoms is replaced by another.

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7
Q

Reduction

A

Removal of oxygen or the gain of hydrogen

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8
Q

Oxidation

A

Removal of hydrogen or the gain in oxygen

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9
Q

Separating funnel

A

The separating funnel allows two reactants to be shaken together and for compounds to be separated based on their solubility or polarity.
E.g. an ester or haloalkane is not soluble in water and will not mix with the aqueous layer. The more dense liquid will be in the lower level, and can be run off by removing the stopper and opening the tap.
The less dense layer is poured off through the top of the separating funnel.

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10
Q

Alkene to a diol (type of reaction and reactants/conditions required)

A

Oxidation reaction

Requires MnO4-/H+ in warm conditions

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11
Q

Alkene to a dihaloalkane (type of reaction and reactants/conditions required)

A

Addition reaction

Br2 or Cl2

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12
Q

Alkene to alkane (type of reaction and reactants/conditions required)

A

Addition reaction
Pt/H2
(platinum catalyst can also be a nickel catalyst)

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13
Q

Alkene to Haloalkane (type of reaction and reactants/conditions required)

A

Addition reaction

HCl/HBr/HX

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14
Q

Haloalkane to alkene (type of reaction and reactants/conditions required)

A

Elimination reaction

KOH (alc)

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15
Q

Alkene to alcohol (type of reaction and reactants/conditions required)

A

Addition reaction

H2O/H+

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16
Q

Alcohol to alkene (type of reaction and reactants/conditions required)

A

Elimination reaction

Conc H2SO4

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17
Q

Alkane to haloalkane (type of reaction and reactants/conditions required)

A

Substitution reaction

Br2/Cl2 and UV light required

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18
Q

Haloalkane to alcohol (type of reaction and reactants/conditions required)

A

Substitution reaction

NaOH or KOH (aq)

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19
Q

Alcohol to haloalkane (type of reaction and reactants/conditions required)

A

Substitution reaction

PCl3, PCl5, SOCl2

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20
Q

Haloalkane to amine (type of reaction and reactants/conditions required)

A

Substitution reaction

NH3(alc)

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21
Q

Amine to alkylmmonium salt (type of reaction and reactants/conditions required)

A

Acid-base reaction

Acid required

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22
Q

Tertiary alcohol goes to … (type of reaction and reactants/conditions required)

A

Nothing occurs when a tertiary alcohol is oxidised (can’t be oxidised)
Reactants are Cr2O72-/H+ or MnO4-/H+

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23
Q

Reduction reaction of tertiary alcohol….

A

This reaction does not occur

Reactants would be NaBH4 (sodium borohydride which is a strong base)

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24
Q

Secondary alcohol goes to ….(type of reaction and reactants/conditions required)

A

Oxidation reaction
Goes to a ketone
Reactants are Cr2O72-/H+ or MnO4-/H+ and heat and reflux

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25
Q

Primary alcohol goes to … (type of reaction and reactants/conditions required)

A

Aldehyde
Distillation
Oxidation reaction
Cr2O72-/H+ or MnO4-/H+ and heat

26
Q

Secondary alcohol goes to ….(type of reaction and reactants/conditions required)

A

Oxidation reaction
Goes to a ketone
Reactants are Cr2O72-/H+ or MnO4-/H+ and heat

27
Q

Ketone goes to … (type of reaction and reactants/conditions required)

A

Secondary alcohol
Reduction reaction
Reactant would be NaBH4 (a strong base)

28
Q

Aldehyde goes to what alcohol….(type of reaction and reactants/conditions required)

A

Primary alcohol
Reduction reaction
NaBH4 (strong base)
Reflux required

29
Q

Aldehyde to carboxylic acid (type of reaction and reactants/conditions required)

A

Oxidation reaction

Cr2O72-/H+ or MnO4-/H+ or Tollens reagent or Benedict’s reagent or Fehling’s reagent

30
Q

Alcohol (which one) to carboxylic acid (type of reaction and reactants/conditions required)

A

Primary alcohol

Reflux conditions with Cr2O72-/H+ or MnO4-/H+

31
Q

Carboxylic acid to carboxylate salt (type of reaction and reactants/conditions required)

A

Acid-base reaction

Base, carbonate or metal is added

32
Q

Carboxylic acid to ester (type of reaction and reactants/conditions required)

A

Substitution reaction
Alcohol in acidic conditions (/H+)
Reflux needed

33
Q

Ester to carboxylic acid (type of reaction and reactants/conditions required)

A

Substitution reaction

H2O/H+

34
Q

Carboxylic acid to acyl/acid chloride (type of reaction and reactants/conditions required)

A

Substitution reaction

PCl3, PCl5 or SOCl2

35
Q

Acyl/acid chloride to carboxylic acid (type of reaction and reactants/conditions required)

A

Substitution reaction

H20

36
Q

Carboxylic acid to amide (primary) (type of reaction and reactants/conditions required)

A

Substitution reaction

NH3 (alc) then heat the salt

37
Q

Amide to carboxylic acid (type of reaction and reactants/conditions required)

A

Substitution reaction

HCl + H2O (H2O/H+) and heat

38
Q

Acid chloride to secondary amide (type of reaction and reactants/conditions required)

A

Substitution reaction

RNH2

39
Q

Acid chloride to primary amide (type of reaction and reactants/conditions required)

A

Substitution reaction

NH3 (alc)

40
Q

Ester to primary amide (type of reaction and reactants/conditions required)

A 
Substitution reaction 
Heat NH3 (alc)
41
Q

Acid chloride to ester (type of reaction and reactants/conditions required)

A

Substitution reaction

Alcohol

42
Q

Ester to carboxylate salt (type of reaction and reactants/conditions required)

A

Substitution reaction

H2O/OH-

43
Q

Condensation reaction

A

A condensation reaction occurs when two molecules join to form a larger molecule and release a smaller molecule(s) in the process. The smaller molecule lost in the reaction is often water, but it can also be methanol, hydrogen chloride, acetic acid or several other molecules.

44
Q

Acid hydrolysis of esters

A

Undergo acid hydrolysis in dilute acid (H+ (aq)) to form a carboxylic acid and an alcohol

45
Q

Basic hydrolysis of esters

A

Undergo RAPID basic hydrolysis in aqueous basic solutions to form an alcohol and the salt of the acid (carboxylate salt)

46
Q

Basic hydrolysis of acid chlorides

A

Does not occur

47
Q

Acidic hydrolysis of acid chlorides

A

Hydrolysis of acid/acyl chlorides produces a carboxylic acid and HCl

48
Q

Acidic hydrolysis of amides

A

Strong acids hydrolyse amides to the corresponding carboxylic acid (and NH4+)
MUST BE H3O+ IN AQUEOUS

49
Q

Basic hydrolysis of amides

A

Strong base will hydrolyse amides to the corresponding acidic salt (carboxylate salt) as well as NH2/amine

50
Q

Acidic hydrolysis of a polyester

A

Produces the dicarboxylic acid and the diol (slower than in alkaline conditions)

51
Q

Basic hydrolysis of a polyester

A

Produces dicarboxylate salt and the diol

52
Q

Acidic hydrolysis of polyamides

A

The products formed will have the N atoms protonated (-NH3+ on both sides) and a dicarboxylic acid will form

53
Q

Basic hydrolysis of polyamides

A

The products formed have an amino group from the N atom (-NH2) and a carboxylate ion forms

54
Q

Acidic hydrolysis of proteins

A

Peptide bond will be broken, N atom is protonated and on the other side of the amino acid a carboxylic acid functional group is produced.
Heat is needed

55
Q

Basic hydrolysis of proteins

A

Peptide bond will be broken, -NH2 on one side and on the other carboxylate ion (- COO-)
Heat is needed

56
Q

Acidic hydrolysis of fats (epic esters)

A

An alcohol and carboxylic acid are produced

57
Q

Basic hydrolysis of fats (epic esters)

A

An alcohol and a carboxylate salt are produced

58
Q

How to purify ester?

A

After the reaction, it will always still have some acid present like sulphuric acid so distillation is needed to get the ester seperate.

59
Q

How to make a polyester?

A

Formed by a repeated condensation (esterification) reaction of a diol and a dicarboxylic acid (or diacid chloride)

60
Q

How to make a polyamide?

A

Formed through a condensation reaction between a diamine and a dicarboxylic acid (or diacidchloride)

61
Q

How to make a polypeptide?

A

Naturally occurring condensation polymers are known as proteins. Amino acids are the basic building blocks of proteins and most have the general formula of RCH(NH2)COOH. (Note - all amino acids are optically active as they have an asymmetric carbon except for glycine)
Proteins are condensation polymers made from many amino acids. The formation of the simplest condensation product between 2 amino acids is called a dipeptide.

62
Q

Esterification reaction

A

Esterification occurs when a carboxylic acid reacts with an alcohol. This reaction can only occur in the presence of an acid catalyst and heat. It takes a lot of energy to remove the -OH from the carboxylic acid, so a catalyst and heat are needed to produce the necessary energy.

CheMYSTERY (4 decks)

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