IB Chem SL

• -ane

• CnH2n+2

• -ene

• CnH2n

• C - - C

• -yne

• CnH2n-2

• C - - - C

• -ol / hydroxy-

• Cn2n+2OH

• - OH

• -al

• CnH2n+1CHO

• -one

• CnH2n+1CO

• -oic acid

• CnH2n+1CO2H

• halo- -ane

• CnH2n+1X

• - X

• -benzene / phenyl-

• C6H5-

• -amide

• CnH2n+1CON

• -amine

• CnH2n+1NH2

• alkyl- / -oate

• CnH2n+1COO

• -nitrile

meth-

eth-

prop-

but-

pent-

hex-

hept-

oct-

non-

dec-

All carbon to carbon bonds are single bonds (Saturated with H atoms)

Contain double or triple bonds

• resists addition reactions

• less reactive, more stable

• less electronegativity differences

• non-polar

• low solubility in water

Carbon atom bonded to functional group is also bonded to one other carbon atom

Carbon atom bonded to functional group is also bonded to two other carbon atoms

Carbon atom bonded to functional group is also bonded to three other carbon atoms

1. Combustion

2. Halogenation

3. Free-Radical Substitution

• excess O2 produces CO2

• limited O2 produces CO or C

• forms alkenes/alkynes

• occurs in UV light

• Steps:

  • Initiation: homolytic fission in UV

  • Propagation: radicals react

  • Terminations: radicals join

• Pair of e- split equally between 2 atoms when a bond breaks

• creates free radical atoms that don’t last long in nature

• 1 atom takes entire e- pair when bond breaks

• creates oppositely charged cation/anion

alkanes that are too long are heated w or w/o a catalyst to produce smaller chains/molecules

1. Hydrogenation

2. Halogenation

3. Polymerization

Hydrogen reacts with alkenes to form alkanes in the presence of a nickel catalyst at 150C

Alkene reacts with halogen gas

Many alkenes join to form a polymer

When a protic acid (HX) is added to an asymmetric alkene, the acidic hydrogen attaches to the carbon w/ most hydrogen substitutes and halide group attaches to the carbon w/ most alkyl substitutes

1. Complete combustion

2. Oxidation

3. Condensation

forms CO2 and H2O

• functional group bonded to primary carbon

• steps:

  • forms aldehyde

  • forms carboxylic acid

• functional group bonded to secondary carbon

• froms a ketone

• functional group bonded to a tertiary carbon

• no oxidation reaction because too much energy needed to break bonds

• K2CR2O7

• Potassium Dichromate (VI)

orange —> green

• alcohol + carboxylic acid = ester + H2O

• reversible

• Catalyzed by H2SO4

• e- seeking, attracted to e- rich species

• cations

• e- rich, attracted to e- deficient species

• lone e- pair, anion

2 reactants combine to form a single product (unsaturated compounds)

1 atom/group of atoms in a compound is replaced by diff atom/group (saturated)

2 reactans join and small molecule is lost in the process (H2O, NH3, HCl)

simplest whole number ratio of atoms in a compound

actual number of atoms in a compound

1. Full structural formula

   • no geometry, shows all bonds

2. Condensed stuctural formula

   • emits bonds, ex. CH3CH3

3. Skeletal formula

   • shows geometric structure, just lines

compound w/ same molecular formula but diff atom arrangement

• diff arrangement of molecules

• diff position of same functional group in molecule

• diff position of atoms give diff functional group in molecule

Distillation separates liquid mixtures based on boiling points. By heating the mixture, the component with the lowest boiling point vaporizes and condenses. It is used in alcohol production and petroleum refining.

• aldehydes have lower boiling point than carboxylic acids and alcohols

• Prevents primary alcohols from becoming carboxylic acid

Continuous heating of reaction mixture to prevent evaporation, maintain constant temperature, and promote desired chemical transformations, commonly used in alcohol oxidation reactions.

• Helps primary alcohols become carboxylic acid by preventing aldehydes from escaping

substitution reactions

1. nucelophilic substitution

• haloalkane —> alcohol

• In a halogenoalkane molecule, the halogen acts as a nucleophile due to its three lone pairs of electrons.

• Carbon atom undergoes heterolytic bond fission with the halogen, where the halogen takes the bonding electrons.

• Often with strong bases like NaOH

• Nucleophilic halogen is replaced by another nucleophilic ion.

• The reaction conditions for this conversion are heat and a dilute solution of sodium or potassium hydroxide.

• In general, halogens react with benzene to form

  chloro-, flouro-, iodo-, bromo- benzene

  chloro-, flouro-, iodo-, bromo- benzene with the byproduct of a hydrogen halide (the halide that benzene reacted with). The catalyst, in general, will be aluminium halide (the halide that reacted with benzene).

• substitution to maintain stability

• electrophilic species attracted to benzene due to ring of delocalized electrons

1. electrophilic substitution (halogenation)

2. Nitration

3. Combustion

• benzene reacts with nitronium ion NO2+

• forms nitrobenzene

• nitronium ion is electrophile

• catalyst: sulfuric acid, H2SO4

• produces CO2 and H2O

If saturated non-cyclic hydrocarbons C-C single bonds are replaced by double/triple/rings

• How many molecules of H2 need to be added to convert the molecule to the corresponding saturated, non-cyclic molecule

• IHD shows how many multiple bonds and rings are present in the molecule

• IHD= (2x+2-y) / 2

  • x—> # C atoms

  • y—> # H atoms

• Group 16 (O and S) = no impact on IHD

• Group 17 (F, Cl, Br, I)= treat as H

• Group 15 (N) = for each N, add one to # of C and H

• # of peaks gives # of different chemical environments in which H atoms are located

• peaks also called signals

Integrated trace goes up in steps that are proportional to the # of H atoms in the chemical environment

all in different chemical environments

• if they are bonded to the same groups = same environment (1 peak)

• if they are bonded to different groups = different environment (2 peaks)

bonds vibrate (stretch/bend) when they absorb IR energy

frequency of IR radiation that’s absorbed

shows natural frequency of chemical bond

• right side: fingerprint region

  • region of infrared spectrum in range of 500 to 1500 cm-1

  • unique for any given compound

  • can be used to find unknown compound

• left side: functional group region

  • gives info about type of bonds present in a molecule

• only polar covalent bonds absorb IR radiation, non-polar ones dont

• intensity is dependent on dipole moment

  • strongly polar bonds = strong bands

  • medium polarity = medium bands

  • weak polarity = weak bands

• Used to determine relative atomic mass (RAM) of an element

• used to determine structure of a compound

• destructive technique due to fragmentation

Ar = (mass/charge)(abundance) + (mass/charge)(abundance) / 100

• highest peak on mass spectrometry graph is created by molecular ion (M+) and is equal to the relative molecular mass of the compound

• subtraction between each peak to find structures fragmenting

double bond = 1

triple bond = 2

ring = 1

radiowaves

proportion of H atoms found in each environment on an H NMR spectrum

solids: fixed shape and volume

liquids: fixed volume, variable shape

gases: variable shape and volume

solid —> gas

liquid —> gas

solid —> gas

gas —> solid

liquid —> solid

gas —> solid

solutions formed by dissolving a solid in a liquid

no new substances produced but states change

ex. ice melting, bromine evaporating, iodine sublimating

formation of new chemical substances: atoms are rearranged in reactants to form new products

in a chemical reaction matter is not created or destroyed

elements and compounds

substance that can’t be broken down into a simpler substance by chemical means