Chapters 20 & 21Chapters 20 & 21

Carbon and HydrocarbonsCarbon and Hydrocarbons

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Other Organic CompoundsOther Organic Compounds

Sect. 20-2: Organic Sect. 20-2: Organic CompoundsCompounds

Organic compoundOrganic compound – covalently bonded – covalently bonded compounds containing carbon (except compounds containing carbon (except carbonates and oxides)carbonates and oxides)

CatenationCatenation – covalent binding of an – covalent binding of an element to itself to form chains or ringselement to itself to form chains or rings

HydrocarbonsHydrocarbons – simplest organic – simplest organic compounds containing only carbon and compounds containing only carbon and hydrogenhydrogen

Structural formulaStructural formula – indicates the – indicates the number and types of atoms present number and types of atoms present in a molecule and also shows the in a molecule and also shows the bonding arrangement of the atomsbonding arrangement of the atoms Condensed structural formulaCondensed structural formula

IsomersIsomers – compounds that have the – compounds that have the same molecular formula but same molecular formula but different structuresdifferent structures

2 types of isomers2 types of isomers

Structural isomersStructural isomers – isomers in – isomers in which the atoms are bonded which the atoms are bonded together in different orderstogether in different orders Example: butane and 2-methylpropaneExample: butane and 2-methylpropane

Geometric isomersGeometric isomers – isomers in – isomers in which the order of atom bonding is which the order of atom bonding is the same, but the arrangement of the same, but the arrangement of atoms in space is differentatoms in space is different Example: 1,2-dichloroetheneExample: 1,2-dichloroethene

In order for geometric isomers to exist:In order for geometric isomers to exist: There must be a rigid structure to prevent There must be a rigid structure to prevent

free rotation around a bondfree rotation around a bond 2 carbons must have at least 2 different 2 carbons must have at least 2 different

groups attached to themgroups attached to them Arrangements have different names, Arrangements have different names,

ciscis and and transtrans cis – cis – same side of the moleculesame side of the molecule transtrans – different side of the molecule – different side of the molecule

Sect. 20-3: Saturated Sect. 20-3: Saturated HydrocarbonsHydrocarbons

Saturated hydrocarbonSaturated hydrocarbon – carbons form – carbons form 4 single covalent bonds with other 4 single covalent bonds with other atomsatoms

AlkaneAlkane – hydrocarbon that contains – hydrocarbon that contains only single bondsonly single bonds Homologous seriesHomologous series – a series in which – a series in which

adjacent members differ by a constant unit adjacent members differ by a constant unit (in the case of alkanes it is 1 C and 2 H)(in the case of alkanes it is 1 C and 2 H)

General formula is CGeneral formula is CnnHH2n+22n+2

CycloalkaneCycloalkane – alkane in which the – alkane in which the carbon atoms are arranged in a ring carbon atoms are arranged in a ring structurestructure Have 2 fewer hydrogens than the Have 2 fewer hydrogens than the

straight chain with the same number of straight chain with the same number of carbonscarbons

Naming rulesNaming rules

1.1. For a straight-chain alkane, use a For a straight-chain alkane, use a prefix telling how many carbons prefix telling how many carbons followed by –ane.followed by –ane.

1 – meth-1 – meth- 6 – hex-6 – hex- 2 – eth-2 – eth- 7 – hept-7 – hept- 3 – prop-3 – prop- 8 – oct- 8 – oct- 4 – but- 4 – but- 9 – non- 9 – non- 5 – pent-5 – pent- 10 – dec- 10 – dec- Example a 5 carbon straight chain Example a 5 carbon straight chain

would be pentanewould be pentane

2.2. Alkyl groups are named by the same Alkyl groups are named by the same prefix as alkanes, but with –yl suffixprefix as alkanes, but with –yl suffix

Alkyl groupAlkyl group – groups of atoms that are – groups of atoms that are formed when a hydrogen is removed from formed when a hydrogen is removed from an alkanean alkane

Attached to “parent chain” to make a branched Attached to “parent chain” to make a branched chain alkanechain alkane

Names of alkyl groups are placed in front Names of alkyl groups are placed in front of the parent chain name and use prefixes of the parent chain name and use prefixes (di, tri, tetra to tell how many of each alkyl (di, tri, tetra to tell how many of each alkyl group are attached)group are attached)

3.3. If multiple alkyl groups exist, list in If multiple alkyl groups exist, list in alpha orderalpha order

4.4. Number the carbons of the parent Number the carbons of the parent chain in such a way that the alkyl chain in such a way that the alkyl groups are on the lowest # carbongroups are on the lowest # carbon

5.5. Include the number carbon that each Include the number carbon that each alkyl group is attached to in the namealkyl group is attached to in the name

6.6. Separate numbers with commas and Separate numbers with commas and numbers from words with dashesnumbers from words with dashes

7.7. When naming a cycloalkane, use When naming a cycloalkane, use the same rules, except add the the same rules, except add the prefix cyclo- in front of the parent prefix cyclo- in front of the parent ring namering name

Sect. 20-4: Unsaturated Sect. 20-4: Unsaturated HydrocarbonsHydrocarbons

Unsaturated hydrocarbonsUnsaturated hydrocarbons – – hydrocarbon in which some carbons hydrocarbon in which some carbons have double or triple bondshave double or triple bonds

AlkeneAlkene – hydrocarbon containing at – hydrocarbon containing at least one double bondleast one double bond General formula is CGeneral formula is CnnHH2n2n

Alkyne – hydrocarbon containing at Alkyne – hydrocarbon containing at least one triple bondleast one triple bond General formula is CGeneral formula is CnnHH2n-22n-2

Rules for multiple bondsRules for multiple bonds All alkane naming rules apply for alkene and All alkane naming rules apply for alkene and

alkyne naming with a few alkyne naming with a few exceptions/additions:exceptions/additions: The parent chain is the longest carbon chain that The parent chain is the longest carbon chain that

contains the multiple bondcontains the multiple bond Instead of –ane suffix, use –ene for double bond Instead of –ane suffix, use –ene for double bond

and –yne for triple bondand –yne for triple bond If there is more than one double or triple bond, If there is more than one double or triple bond,

use di or tri just before the suffix to indicate how use di or tri just before the suffix to indicate how many double/triple bondsmany double/triple bonds

Carbons should be numbered so that the multiple Carbons should be numbered so that the multiple bond has the lowest number possible & the bond has the lowest number possible & the number of the carbon attached to the multiple number of the carbon attached to the multiple bond is indicated just before the parent chain’s bond is indicated just before the parent chain’s name (ex: 1-pentene)name (ex: 1-pentene)

Chapter 21Chapter 21Sect. 21-1&2: Functional Sect. 21-1&2: Functional

Groups and Classes of Groups and Classes of Organic CompoundsOrganic Compounds

Functional groupFunctional group – an atom or group of – an atom or group of atoms that is responsible for the specific atoms that is responsible for the specific properties of an organic compoundproperties of an organic compound AlcoholsAlcohols Alkyl halidesAlkyl halides EthersEthers AldehydesAldehydes KetonesKetones Carboxylic acidsCarboxylic acids EstersEsters

AlcoholAlcohol – organic compounds that – organic compounds that contain one or more hydroxyl groupscontain one or more hydroxyl groups

Naming alcohols:Naming alcohols: The parent chain must contain the The parent chain must contain the

hydroxyl group; # so it has lowest #hydroxyl group; # so it has lowest # Replace the final –e in the name with –ol Replace the final –e in the name with –ol

or if more than one hydroxyl group, use or if more than one hydroxyl group, use the whole name and then diol (2) or triol the whole name and then diol (2) or triol (3), etc.(3), etc.

Indicate which # carbon the hydroxyl Indicate which # carbon the hydroxyl group is attachedgroup is attached

Alkyl halidesAlkyl halides – organic compounds in which – organic compounds in which one or more halogen atoms (F, Cl, Br, or I) are one or more halogen atoms (F, Cl, Br, or I) are substituted for one or more hydrogen atomssubstituted for one or more hydrogen atoms

Naming alkyl halides:Naming alkyl halides: Parent chain must include halideParent chain must include halide Add prefix indicating which halide is attached and if Add prefix indicating which halide is attached and if

necessary, add prefix to indicate how manynecessary, add prefix to indicate how many Indicate the # carbon to which the halide is Indicate the # carbon to which the halide is

attachedattached EthersEthers – organic compound in which two – organic compound in which two

hydrocarbon groups are bonded to the same hydrocarbon groups are bonded to the same atom of oxygenatom of oxygen

Naming ethersNaming ethers The word ether will come at the end of the nameThe word ether will come at the end of the name List the alkyl groups in alpha order in front of List the alkyl groups in alpha order in front of

“ether” and use di if they are the same and put “ether” and use di if they are the same and put spaces between each wordspaces between each word

AldehydeAldehyde – organic compound in which – organic compound in which the carbonyl group is attached to a the carbonyl group is attached to a carbon atom at the end of a carbon carbon atom at the end of a carbon chainchain To name, change the end –e to -alTo name, change the end –e to -al

KetoneKetone – organic compound in which – organic compound in which the carbonyl group is attached to a the carbonyl group is attached to a carbon atom within the chaincarbon atom within the chain To name, chage the end –e to –one and To name, chage the end –e to –one and

identify which carbon the ketone is identify which carbon the ketone is attached toattached to

Carboxylic acidCarboxylic acid – an organic compound that – an organic compound that contains the carboxyl functional groupcontains the carboxyl functional group To name, change end –e to –oic acid; if more than To name, change end –e to –oic acid; if more than

one use dioic acid (2) or trioic acid (3), etc. one use dioic acid (2) or trioic acid (3), etc. EsterEster – an organic compound with carboxylic – an organic compound with carboxylic

acid group in which the hydrogen of the acid group in which the hydrogen of the hydroxyl group has been replaced by an alkyl hydroxyl group has been replaced by an alkyl groupgroup To name, name the carboxylic acid that it was To name, name the carboxylic acid that it was

formed from and then change the –oic acid to –oateformed from and then change the –oic acid to –oate Name the alkyl group that replaced the hydrogen & Name the alkyl group that replaced the hydrogen &

add to front of nameadd to front of name