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Fundamentals Of Chemistry > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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1
Q

What is organic chemistry?

A

Concerned with compounds of carbon

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2
Q

What do organic compounds contain?

A

Carbon, hydrogen and sometimes oxygen and other non-metallic elements

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3
Q

What order are formulas for organic compounds written?

A

Carbon
Hydrogen
Then any others

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4
Q

Features of carbon?

A

Can form an infinite number of compounds
Can make up to four covalent bonds (single, double or triple)
Can form covalently linked C-C chains of unlimited length
Forming a variety of branches, linear and cyclic compounds

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5
Q

Name of linear hydrocarbons?

A

Aliphatic

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6
Q

Name of branched hydrocarbons?

A

Alicyclic

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7
Q

Name of ring shape hydrocarbons?

A

Aromatic

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8
Q

How can carbon skeletons vary?

A

Length
Branching
Double bind positions (if present)
Presence of rings

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9
Q

Homologous series definition?

A

A group of organic chemical compounds, that have similar structure and properties, the structure only differs by the number of CH2 units in the main carbon chain

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10
Q

Arrangement of bonds carbon can form?

A

4 single bonds
2 double bonds
2 single bonds and 1 double bond
1 single bond and 1 triple bond

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11
Q

What is the alkane formula?

A

C(n)H(2n+2)

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12
Q

Alkanes end in the suffix of?

A

Ane (methane, ethane, propane)

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13
Q

Alkane structure?

A

Hydrocarbons
Only have single C-C bonds
Saturated (have maximum number of hydrogens)

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14
Q

How are unbranched alkanes named?

A

The pre-fix of the number of carbons in chains followed by ‘ane’

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15
Q

How are branched alkanes named?

A

1) identify the longest carbon chain in any direction
2) number the carbon chain (make sure the branched group has the lowest number possible)
3) find the name of of longest chain e.g. octane
4) find the name of the branched group e.g. meth and add ‘yl’
5) find the number of the carbon the branch group is on
6) e.g. 2-methyloctane
7) write in alphabetical order if more than one branch group

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16
Q

Number of carbon chains and names for alkanes?

A

1) meth
2) eth
3) prop
4) but
5) pent
6) hex
7) hept
8) oct
9) non
10) dec

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17
Q

What is the name of a branch off of a alkane?

A

Alkyl group

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18
Q

What is a halogenoalkane?

A

Where one or more hydrogen from an alkane is replaced by a halogen
Name added to alkane with number of branch

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19
Q

What state are the first 4 alkanes at room temperature?

A

Gas

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20
Q

What state are alkanes 5-8 at room temperature?

A

Liquid

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21
Q

Alkane properties in terms of boiling point?

A

The longer the carbon chain the higher the boiling point as the chain increases so does the number of electrons in the molecules so the van der Waals forces are stronger
Straight alkanes have higher boiling points that branches alkanes as the molecules can lie closer together

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22
Q

Alkene structure?

A

End in ‘ene’
Have at least one C-C double bond
Unsaturated (doesn’t have maximum number of hydrogen atoms)

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23
Q

What is the alkene formula?

A

H(n)C(2n)

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24
Q

Alkyne structure?

A

End in ‘yne’
Contain at least one C-C triple bond
Unsaturated

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25
Q

Naming alkenes/alkynes

A

1) The longest carbon chain must contain the double/triple bond
2) number carbon chain from the end closest to double/triple bond
3) add number to name of the carbon the double bond is on
4) add any groups e.g. methyl

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26
Q

How to test if alkane or alkene?

A

Use bromine water
Becomes colourless if alkene as bromine reacts with C-C double bond
Stays red/brown if alkane as no double bond to react with

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27
Q

What is hydrogenation?

A

A reaction in which hydrogen atoms add to each of the carbon atoms in a double bond of an alkene turning it into an alkane
A metal catalyst is used

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28
Q

What is a cycloalkane?

A

A ring of carbon atoms with two hydrogen atoms attached to each carbon
Formula of C(n)H(2n)
They are saturated
Add cyclo to the name

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29
Q

What is an arene?

A

Group of aromatic hydrocarbons with a molecular structure containing one or more flat sets of six carbon atoms. Each carbon forms a single covalent bond to the carbons either side and to one hydrogen atom. The final unpaired electron on each carbon is located in the P-orbital that sticks out above and below the plane of the ring. This forms a ring of delocalised electrons.
Unsaturated cyclic hydrocarbons
Benzene is an example

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30
Q

Structure of benzene?

A

Molecular formula of C6H6
Ring structure
Groups can be added off of benzene

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31
Q

What is the displayed formula?

A

Shows the arrangement of atoms and the bonds

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32
Q

What are isomers?

A

Compounds with the same molecular formula but the atoms are arranged differently which can lead to differences in physical and chemical properties

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33
Q

Types of structural isomers?

A

Chain length isomers
Position isomers
Functional group isomers

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34
Q

Types of stereoisomers?

A

Geometric isomers
Optical isomers

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35
Q

What are chain length isomers?

A

Carbon atoms in skeleton arranged differently

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36
Q

What are positional isomers?

A

Have the same functional groups but attached to different points of the main chain

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37
Q

What are functional group isomers?

A

Have different functional groups
E.g. alkane, alkene, alcohol, ether

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38
Q

What is a stereoisomer?

A

Have the same structural formula but different in the arrangement of bonds

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39
Q

What is cis-trans isomerism?

A

Differ in the arrangement of the groups attached to the carbons in double bonds

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40
Q

What are sigma bonds?

A

End to end overlap of atomic orbitals
All single bonds

41
Q

What are Pi bonds?

A

When the lobe of one atomic orbital overlaps another
Double bonds have a Pi bond as wells as a sigma bond

42
Q

What is the difference between cis and trans isomers?

A

If the atoms other than hydrogen are all on the same side of the chain they are cis isomers

If the atoms other than hydrogen are different sides of the chain they are trans isomers

43
Q

Limitation of cis-trans isomerism?

A

Hard to figure out which side of which if lots of hydrogens have been substituted for different groups
E.g. one side may have carbon and chlorine and the other fluorine and bromine

44
Q

What is E-Z isomerism?

A

Used to identify stereoisomers that cannot be defined at cis or trans
Isomers identified as either E or Z
The higher the atomic number the higher the priority
E corresponds to trans form (opposite sides)
Z corresponds to cis form (same sides)

45
Q

What is optical isomerism?

A

Have the same molecular and structural formula but cannot be superimposed as they are mirror images
Can occur when an asymmetric carbon (bonded to four different groups) is present so it forms a chiral centre of the molecule

46
Q

What is a chiral centre?

A

When a carbon atoms is bonded to four different groups

47
Q

How to tell the type of optical isomer?

A

Can rotate the plane of polarised light.
Clockwise - positive enantiomer (D form)
Anti-clockwise- negative enantiomer (L form)
No effect- racemic/racemate

48
Q

What is R and S configuration?

A

Assign priority to all groups from chiral centre by atomic number
View molecule so lowest priority is away from observer
Arrow is drawn around in order of priority groups
If arrow is clockwise it is R form
If arrow is anti-clockwise it is S form

49
Q

How are halogenoalkanes made?

A

Free radical substitution

50
Q

How are halogenoalkenes made?

A

Electrophilic addition

51
Q

What are the three key steps of free radical substitution?

A

1) initiation
2) propagation
3) termination

52
Q

What is initiation in free radical substitution?

A

UV light absorbed by halogen molecule to provide energy to break the bond. One electron goes to each halogen and forms two free radicals (homolytic fission)

53
Q

What is homoloytic fission?

A

Single bond breaks, one electron to each molecule. Shown by a curly half arrow head. Forms two products that are the same

54
Q

What is heterolytic fission?

A

Breaking of bonds. One atoms gains both electrons. So atom is now negatively charged and other is positively charged. Two different products

55
Q

What is a free radical?

A

A highly reactive species with a single unpaired electron. Electron is represented by a dot.

56
Q

What is propagation in free radical substitution?

A

A halogen radical reacts with a methane molecule. This removed hydrogen from the methane and forms a methyl radical and hydrogen chloride. The methyl radical can then bond with a halogen molecule forming another halogen radical and halogenmethane. During this process the total number of radicals remains the same.

57
Q

What is termination in free radical substitution?

A

Total number of free radicals decreases. Free radicals can join together to create stable molecules.
Methyl to halogen
Halogen to halogen
Methyl to methyl

58
Q

Why is the process of synthesising halogenoalkanes by reacting alkanes with a halogen not cost effective?

A

Hard to separate the mixture of products formed

59
Q

What are chlorofluorocarbons?

A

Halogenoalkane molecules where all the hydrogen atoms have been replaced by fluorine or chlorine.

60
Q

Why are chlorofluorocarbons bad?

A

Destroy the ozone layer (O3) due to free radical substitution

61
Q

How are halogenoalkanes formed from alkanes?

A

Electrophilic addition. As the double bond is an area of high negative charge making it very reactive.UV light is not needed.

62
Q

What is an electrophile?

A

Electron pair acceptor. They accept a pair of electrons to form a covalent bond. They are electron deficient. Represented as E+.

63
Q

What is a nucleophile?

A

Electron pair donator. They donate a pair of electrons to form a covalent bond. They can be represented by Nu:

64
Q

What is the electrophilic addition mechanism?

A

The double bond in the alkene is electron dense (negatively charged). The electrophile is attracted to this. The electrophile breaks down and undergoes heterolytic fission so both the electrons go to the atom not attaching to the double bond. Finally the atom that accepted the electrons bonds with the other carbon to form a dative covalent bond.

65
Q

What are alcohols?

A

Homologous series of organic compounds with the general formula CnH2n+1OH
Names end in ol
Functional group is OH

66
Q

How to name alcohols?

A

Name of length of carbon chain with suffix -ol
If there are 3 or more carbons positional isomerism can be displayed
The carbon number the OH is attached to is written before -ol

67
Q

Properties of alcohols?

A

Much higher boiling point than alkanes
Boiling point increases as carbon chain length increases
Most are liquid at room temperature

68
Q

Explaining properties of alcohols?

A

The electronegative oxygen atom in the hydroxyl group means alcohols are polar so can take part in hydrogen bonding meaning the boiling point will be higher than that of an alkane
Hydrogen bonding also means alcohols can mix with water

69
Q

How can alcohols be produced?

A

Hydration of an alkene
add water to alkene in form of steam with a phosphoric acid catalyst. Temperature must be 570K and pressure 60-70 atm

Fermentation
Glucose + yeast —> ethanol + carbon dioxide
Anaerobic conditions
Temperature 25-35c
Yeast dies when ethanol concentration reaches around 15%
Slow process

70
Q

Advantages of fermentation?

A

Renewable resources used
Less energy used

71
Q

Advantages of hydration?

A

High yield of ethanol
Atom economy of 100%
Fast reaction
Can be done continuously

72
Q

Types of alcohols?

A

Primary: have one R group attached to the carbon to which the OH group is attached
Secondary: have two R groups attached to the carbon to which the OH group is attached
Tertiary: have two R groups attached to the carbon to which the OH group is attached

73
Q

Function group of aldehyde and ketones?

A

Carbonyl group C=O

74
Q

Formula of aldehydes and ketones?

A

CnH2nO

75
Q

Differences between aldehydes and ketones?

A

Carbonyl group at the end is an aldehyde. So it has at least one hydrogen attached to it

Carbonyl group in the middle is a ketone so has two carbons attached to it

76
Q

How to name aldehydes?

A

Named using carbon chain length and then the suffix -al
Carbons numbered starting with carbonyl group as 1

77
Q

How to name ketones?

A

Using length of carbon chain and suffix -one
Carbon number of carbonyl group placed before suffix

78
Q

Reactivity of the carbonyl group?

A

Polar
Positive charge on the carbon makes it open to attacked by nucleophiles
Aldehydes and ketones can be reduced, forming alcohol
Aldehydes can be oxidised to carboxylic acids

79
Q

Properties of aldehydes and ketones?

A

Small ones are soluble in water due to hydrogen bonding between a lone pair on the oxygen of the carbonyl group and the hydrogen of water
As size increases solubility decreases due to interference in hydrogen bonding by the hydrocarbon tails
Have mid range boiling points as have van der Waals forces AND the polar carbonyl group means dipole-dipole interactions are present

80
Q

Comparing boiling points of alkanes, ketones & aldehydes, alcohols and carboxylic acids?

A

Alkanes have the lowest as only van der Waals forces are present

Aldehydes & ketones are higher as they also have dipole-dipole interactions as the carbonyl group is polar

Alcohols are higher still as they also have hydrogen bonding

Carboxylic acids are highest as they have more hydrogen bonds

81
Q

How are aldehydes produced?

A

Primary alcohols can be oxidised by an oxidising agent such as an aqueous solution of acidified potassium dichromate which changes colour from orange to green. Water is also produced in the reaction.

82
Q

How are ketones produced?

A

Secondary alcohols can be oxidised by an oxidising agent such as an aqueous solution of acidified potassium dichromate. Water is also produced

83
Q

Why are tertiary alcohols resistant to oxidation?

A

The lack of hydrogen atoms on the carbon atom to which the hydroxyl group of attached

84
Q

How to test whether aldehyde or ketone?

A

Tollens’ reagent:
Sodium hydroxide + aqueous silver nitrate. This forms a brown precipitate of silver nitrate (Ag2O). Aqueous ammonia is added until precipitate dissolves and a solution of the silver amine [Ag(NH3)2]+ is formed.
A silver colour is formed if aldehydes are present
No colour change if ketone

Benedict’s solution:
An alkaline solution containing copper ions.
When heated with an aldehyde the Cu2+ complex ion acts as an oxidising agent and the blue turns to red
No colour change if ketone

85
Q

Functional group of carboxylic acids?

A

Carboxyl group (COOH) attached to terminal carbon

86
Q

How to name carboxylic acids?

A

Using length of carbon chain and suffix -oic acid

87
Q

Reactivity of carboxylic acids?

A

Polar due to presence of two electronegative oxygen atoms and a partially charged carbon and hydrogen atom
Can take part in:
Neutralisation- carboxylic acid loses a proton to from a carboxylate salt
Nucleophillic substitution- partially positive carbon is attacked by nucleophile resulting in substitution of OH group
Esterification- reaction with an alcohol for form an ester

88
Q

Properties of carboxylic acids?

A

Solubility depends on side. The smaller the compound the higher the solubility.

Carboxylic acids are higher due to more hydrogen bonds present

89
Q

How are carboxylic acids formed?

A

Primary alcohols are reacted with an excess of oxidised agent and refluxed.
Primary alcohol—>aldehyde
—>carboxylic acid
Reflux position is the condenser tube vertical. The condenser tube is continuously surrounded by cold water. As aldehyde is produced it evaporates but the cold water then cools it back to a liquid so it can go back to undergo second oxidisation
Reflux definition: the continuous evaporation and condensation of a volatile substance without loss of any product

90
Q

Functional group of esters?

A

-COO-
Carbon double bonded to one oxygen and single bonded to another oxygen

91
Q

How is an ester formed?

A

Esterification:
When alcohol is warmed with a carboxylic acid in the presence of an acid catalyst. A water molecule is removed
Concentrated sulfuric acid is often used as the catalyst
The O-H bond of alcohol is broken and water formed with the OH from the carboxylic acid group and the H in the alcohol group

Carboxylic acid + alcohol -> ester + water

92
Q

Naming esters?

A

First part from the alcohol used with -yl e.g ethyl
Second part from carboxylic acid used with -anoate e.g. ethanoate

X-yl X-anoate

93
Q

Hydrolysis of esters?

A

Chemical reaction using water to break down bonds of a substance
Esters can be hydrolysed by refluxing with either an acid or alkali
With an acid it reverses the ester back to an alcohol and carboxylic acid
With an alkali it hydrolysed to an alcohol and sodium salt of the acid

94
Q

What is an amine?

A

Nitrogen containing organic compounds derived from ammonia where one or more of the hydrogen atoms has been replaced by an alkyl or aryl group

95
Q

Types of amines?

A

Primary: where one hydrogen from ammonia is substituted with carbon
Secondary: where two hydrogens from ammonia are substituted
Tertiary: where all three hydrogen atoms are substituted
Quaternary: where four carbons are attached to the nitrogen, using ammonia’s lone pair of electrons

96
Q

Naming amines?

A

Use the length of the carbon chain and use suffix -amine
E.g. methylamine

If other functional groups are present then the amino- prefix is used
E.g. 2-aminoethanoic acid

97
Q

Properties of amines?

A

Solubility: shorted chains are soluble in water as the lone pair of electrons in the nitrogen atom allows them to form hydrogen bonds with water molecules
Larger amines are less soluble as the larger R groups interfere with hydrogen bonds

Boiling points: primary amines have higher boiling points that alkanes as they can form hydrogen bonds .
Secondary amines having slightly lower boiling points as the nitrogen forming the hydrogen bond is in the middle of the chain and this slightly reduces the strength of the dipole
Tertiary amines have even lower boiling points

98
Q

What is an amide?

A

Products of reactions between carboxylic acids and amines

An amide and water is produced

Contain functional group CONH

Amino acids contain both amine and carboxylic acid functional groups. They can react together to form an amide link (peptide bond)

Fundamentals Of Chemistry (10 decks)

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