Hein's Flashcards (copy)

Compounds composed of only carbon and hydrogen

a hydrocarbon containing only single covalent bonds that form a homogenous series

CnH2n+2

a series of compounds with the same general formula, but differing form each other by a common structural unit

single C-C bonds in a ring

prop-

but-

Suffix: -ane General Formula: C(n)H(2n+2)

Functional group: alkenyl Suffix: -ene General Formula: C(n)H(2n)

Functional group: Alkynyl Suffix: -yne General Formula: C(n)H(2n-12)

Functional group: Hydroxyl Suffix: -ol General Formula: C(n)H(2n+1)OH

Functional group: ether Suffix: -oxyalkane General Formula: R-O-R'

Functional group: Aldehyde (carbonyl) Suffix: -anal General Formula: R-CHO

Functional group: Carbonyl Suffix: -anone General Formula: R-CO-R'

Functional group: Carboxyl Suffix: -anoic acid General Formula: C(n)H(2n+1)COOH

Functional group: ester Suffix: -anoate General Formula: R-COO-R'

Functional group: carboxyamide Suffix: -anamide

Functional group: amine Suffix: -anamine (if more than one functional group amino infront)

Functional group: nitrile Suffix: -anenitrile

Functional group: Phenyl Suffix: -benzene

-C6H5

addition of a halogen Name: Fluoro-, Chloro-, bromo-, iodo- General Formula: CnH(2n+1)X (where X = halogen)

Compounds with the same molecular formula but atoms and functional groups attached in different ways

• similar chemical properties

• Physical properties may differ

• 1 R group

• 2 hydrogen atoms

• 2 R groups

• 1 Hydrogen atom

• 3 R groups

• no hydrogen atoms

C6H6

instead of creating discrete alternating π bonds the p orbital overlaps meaning the π bonds are shared by all six carbon, forming a delocalized π electron cloud which the electrons are concentrated in two donut shapes above and below the plane of the ring which is very stable

ring structure consisting of alternating single and double carbon-carbon bonds

a physical separation process that uses differences in boiling points to separate the mixture into fractions of similar boiling point.

boiling point increases as the carbon chain becomes longer

a measure of how readily a substance vaporizes

Volatility increases with molar mass

straight-chain isomers have stronger intermolecular forces so branched chains have a lower boiling point

contains only single bonds between carbon atoms EX. Alkanes

has at least one double or triple bond EX. Alkenes and Arenes

compounds which do not contain a benzene ring, may be saturated or unsaturated EX. Alkanes and Alkenes

compounds which contain a benzene ring, they are all unsaturated compounds EX. Benzene and Phenol

• an electron-deficient species which is therefore attracted to parts of molecules which are electron rich

• are positive ions or have a partial positive charge (act as a lewis acid and accept protons)

• NO2+, H+, Brδ+

• an electron rich species which is therefore attracted to parts of molecules which are electron deficient

• have a lone pair of electrons and may also have a negative charge

• They act as a lewis base and donate a pair of electrons to form a new covalent bond

• Examples: Cl-, OH-, NH3, H2O, CN-

hydrocarbon + oxygen --> carbon dioxide + water

• Occurs when two reactants combine to form a single product

• Characteristic of unsaturated compounds

• occurs when one atom or group of atoms in a compound is replaced by a different atom or group

• Characteristic of saturated compounds aromatic compounds

• occurs when two reactions join together (addition) and in the process a small molecule such as H2O, HCl, or NH3 is lost (elimination)

• reaction occurs between functional group in each reactant

• is when a covalent bond breaks by splitting the shared pair of electrons between the two products

• produces two free radicals, each with an unpaired electron

• is when a covalent bond breaks with both the shared electrons going to one of the products

• produces two oppositely charged ions

Atoms or groups that leaves the parent chain

occurs in unsaturated fats

Must be balanced and can be different

1. Initiation

2. Propagation

3. Termination

UV light supplies the energy necessary to break the relatively week halogen bond (Ex. Cl-Cl) homolytically to form halogen free radicals (chlorine free radicals)

1. Free radicals (Chlorine) contain an unpaired electron are very energetic so they react with an alkane (Ex. Methane) to remove a hydrogen atom forming hydrogen halogen and propagating another free radical

2. Alkane radical (Ex. Methyl Radical) reacts with another halogen to produce a halogenoalkane and another halogen radical so propagation can continue

Radical reactions can be terminated by

• Escaping from the system

• colliding with the walls

• reacting with radicals

Added: Hydrogen gas Catalyst: Nickel at 150°C Conversion: Alkene to alkane

Added: Halogen gas (Chlorine, Bromine, iodine) Catalyst: None Conversation: Alkene to dihalogenoalkane

Addition across a double bond. If there is double bond present in the solution, then the addition react will occur and the final solution will be completely clear. If not, the solution will remain an orange color after the bromine solution is added

Added: Hydrogen Halide (HCl, HBr) Catalyst: No Conversation: Alkene to halogenoalkane

HI more reactive than HBr which is more reactive than HCl

Added: H2O (water) Catalyst: H2SO4 (concentrated) and steam heated Conversation: Alkene to Alcohol

in certain situations alkenes can break their double bond and add themselves together to produce long chains known as addition polymers which contain thousands of monomers

Alcohol + oxygen --> carbon dioxide + water complete combustion

Added: Potassium Dichromate (K2Cr2O7) or simply [O] Catalyst: Heated and distilled Conversation: Alcohol to Aldehyde

• aldehydes have a lower boiling point than carboxylic acids due to their lack of hydrogen bonds which means that in a distillation column they get tapped off

Added: Potassium Dichromate (K2Cr2O7) or simply [O] Catalyst: Reflux Heated Conversation: Alcohol to Carboxylic acid Color Change: orange to green

By refluxing to expose the aldehyde to the oxidizing agent for a prolonged period of time

is a technique that involves the cyclic evaporation and condensation of a volatile reaction mixture, preserving the solvent as it does not evaporate

Added: Potassium Dichromate (K2Cr2O7) or simply [O] Catalyst: Reflux Heated Conversation: Alcohol to ketone (2 H atoms removed) Color Change: orange to green

no reaction so no color change as it would involve the breaking of the carbon skeleton which requires significantly more energy

Added: Carboxylic acid Catalyst: Concentrated H2SO4 (Sulfuric acid) Conversation: Alcohol to ester

with the exception of fluoroalkanes halogenoalkanes are more reactive than alkanes as the carbon and halogen bond is weaker than C-C and C-H, but do not burn as readily

carbon-halogen bond is polar so the electron deficient carbon is open to be attacked by a nucleophile

does not readily undergo addition reactions as an additional 150 kJ mol^-1 of energy is required to overcome the delocalization energy, but electron deficient species which are electrophiles (positive or slightly positive (δ+)) are attracted to the electron above and below the ring, thus substituting a hydrogen atom

Added: Nitric acid (HNO3) Catalyst: Concentrated H2SO4 (Sulfuric acid) and heat Conversation: New aromat and water

Added: Br2 Catalyst: Aluminium Tribromide (AlBr3) Conversation: New aromat and Hyrdogen halide

A type of substitution reaction in which a nucleophile is attracted to an electron-deficient centre or atom, where it donates a pair of electrons to form a new covalent bond.

depends on the concentration of the halogenoalkane and the nucleophile

depends only on the concentration of the halogenoalkane

an Sn2 mechanism

• substitution nucleophilic bimolecular

• 1 step

• 2 molecules in the rate determining step

• primary alcohol

when a nucleophile attacks the electron deficient carbon from the opposite side of the leaving group

1. curly arrow from nucleophiles lone pair of negative charge terminating at the carbon atom

2. curly arrow from the bond between the carbon and halogen, ending at the halogen (leaving group)

3. Partial bonds represented by dotted lines make up the transition state which is enclosed by square brackets with a single negative charge

4. Formation of product and leaving group shown

large bulky groups prevent the mobility of a nucleophile

an Sn1 mechanism

Step 1: Heterolytic breaking of the carbon-halogen bond creating a halide ion and a carbocation intermediate Step 2: Nucleophile attaches to the carbocation

Electron donation or withdrawal through the sigma bonds of a molecule.

1. curly arrow from carbon-halogen bond to the halogen leaving group

2. representation of the carbocation which clearly shows a positively charged central carbon atom

3. curly arrow from the nucleophiles lone electron pair or negative charge, terminating at the carbon atom

4. formation of the product and leaving group must be shown

both Sn2 and Sn1

1. Type of halogenoalkane

2. Nature of the halogen

3. Choice of Solvent

Tertiary > Secondary > Primary

C-I bond is weaker than the C-Br bond which is in-turn weaker than the C-Cl bond, so iodine is a better leaving group as less energy is required and it occurs faster

• Sn2 reactions favor aprotic, polar solvents

• Sn1 reactions favor protic, polar solvents

• don't possess OH or NH group so they can't for a hydrogen bond with the nucleophile

• Doesn't solvate the nucleophile allowing it to maintain its properties

• are polar

• possess an OH or NH group so they can for a hydrogen bond with the nucleophile

• solvates the nucleophile allowing it to attack electrophiles such as the δ+ carbon

does not contain a hydrogen ion

contains a hydrogen ion

process by which solvent molecules surround the dissolved ions

• strong charge

• negatively charged particles (OH-) are better nucleophiles than polar substances (H2O)

alkenes contain an electron cloud, created by the pi bond 90° to the plane of the sigma bonds, which is attracts electrophiles

Addition of an electrophile to a carbon-carbon double bond to yield a saturated product

1. curly arrow from carbon-carbon bond to the positive section

2. curly arrow from the bond in the added substance ending in negative section

3. curly arrow from lone pair or negative charge to C+ (carbocation)

4. Structural formula shown of product

as the halogen approaches the electron rich C=C bond of the alkene electrons within the halogen molecule are repelled, resulting in a temporary dipole