Chapter 11 - Basic Concepts of Organic Chemistry Flashcards
what is a hydrocarbon?
a compound containing carbon and hydrogen only
what is the structural formula of methane?
CH4
what is the structural formula of but-2-ene?
CH3CHCHCH3
what is a saturated hydrocarbon?
a hydrocarbon with only single bonds
what is an unsaturated hydrocarbon?
a hydrocarbon with carbon-carbon multiple bonds (e.g. double bonds or triple bonds)
what is a homologous series?
a family of compounds with similar chemical properties whose successive members differ by the addition of a -CH- group
what are the first 3 members of the alkane homologous series?
methane, ethane, propane
what is a functional group?
the part of the organic molecule that is largely responsible for the molecule’s chemical properties
why does carbon form a large number of compounds?
- carbon is in group 4 (14) of the periodic table, with 4 electrons in its outer shell
- each carbon atom can form 4 covalent bonds to other atoms
- these can be single, double, and even triple bonds
- carbon atoms can bond to other carbon atoms to form long chains
what are the 3 classifications of hydrocarbons?
- aliphatic - carbon atoms are joined to each other in unbranched (straight) chains, branched chains, or non-aromatic rings
- alicyclic - carbon atoms are joined to each other in ring (cyclic) structures, with or without branches
- aromatic - some or all of the carbon atoms are found in a benzene ring
what are the three homologous series of aliphatic hydrocarbons? (that you should be aware of)
- alkanes - containing single carbon-to-carbon bonds
- alkenes - containing at least one double carbon-to-carbon bond
- alkynes - containing at least one triple carbon-to-carbon bond
what does the stem of the name of an organic molecule indicate?
the number of carbon atoms in the longest continous chain in the molecules
what does the prefix of the name of an organic molecule indicate?
the presence of side chains or functional groups
what does the suffix of the name of an organic molecule indicate?
functional groups
what are the steps for naming aliphatic alkanes?
- all alkanes have the suffix -ane
- identify the longest chain of carbon atoms and name it
- identify any side chains attached to the parent chain. these are known as alkyl groups. the name of an alkyl group is added as a prefix to the name of the parent chain
- add numbers before the alkyl groups to show the position of the alkyl groups on the parent chain
what is the stem for a compound with 1 carbon atom?
meth-
what is the stem for a compound with 2 carbon atoms?
eth-
what is the stem for a compound with 3 carbon atoms?
prop-
what is the stem for a compound with 4 carbon atoms?
but-
what is the stem for a compound with 5 carbon atoms?
pent-
what is the stem for a compound with 6 carbon atoms?
hex-
what is the stem for a compound with 7 carbon atoms?
hept-
what is the stem for a compound with 8 carbon atoms?
oct-
what is the stem for a compound with 9 carbon atoms?
non-
what is the stem for a compound with 10 carbon atoms?
dec-
how do you name cyclic alkanes?
the same rules apply as when naming aliphatic alkanes, but the prefix cyclo- in front of the stem is used
how are alkenes named?
using the same rules as for alkanes, except the suffix is -ene
the position of the C=C bond in the chain must be stated for alkenes that have 4 or more carbon atoms in the longest chain
how do you name compounds containing functional groups?
the same basic principles apply as for naming alkanes
1. identify the longest unbranched chain of carbon atoms
2. identify any functional groups and any alkyl side chains, and select the appropriate prefixes/suffixes for them
3. number any alkyl groups and functional groups to indicate their position on the longest unbranched chain
what is the functional group and prefix/suffix for alkenes?
functional group: C=C
suffix: -ene
what is the functional group and prefix/suffix for alcohols?
functional group: -OH
prefix: hydroxy-
suffix: -ol
what is the functional group and prefix/suffix for haloalkenes?
functional groups: -Cl, -Br, -I
prefix: chloro-, bromo-, iodo-
what is the functional group and prefix/suffix for aldehyde?
functional group: -CHO
suffix: -al
what is the functional group and prefix/suffix for ketones?
functional group: -C(CO)C-
suffix: -one
what is the functional group and prefix/suffix for carboxylic acids?
functional group: -COOH
suffix: -oic acid
what is the functional group and prefix/suffix for esters?
functional groups: -COOC-
suffix: -oate
what is the functional group and prefix/suffix for acyl chloride?
functional group: -COCl
suffix: -oyl chloride
what is the functional group and prefix/suffix for amines?
functional group: -NH2
prefix: amino-
suffix: -amine
what is the functional group and prefix/suffix for nitriles?
functional group: -CN
suffix: -nitrile
what is molecular formula?
- the molecular formula shows the number and type of atoms present in a molecule
- it does not show how the atoms are joined together so different molecules can have the same molecular formula
what is empirical formula?
empirical formula is the simplest whole-number ratio of the atoms of each element present in a compound
what is general formula?
the simplest algebraic formula for any member of a homologous series
what is displayed formula?
displayed formula shows the relative positioning of all of the atoms in a molecule and the bonds between them
what is structural formula?
the structural formula uses the smallest amount of detail necessary to show the arrangement of the atoms in a molecule. it shows clearly which groups are bonded together
what is skeletal formula?
a simplified organic formula where you remove all of the hydrogen and carbon labels and any bonds to hydrogen atoms
in skeletal formula:
- a line represents a single bond
- an intersection of two lines represents a carbon atom
- the end of a line represents a CH3 group
are functional groups included in skeletal formula?
when functional groups are present in a molecule, they must be included in the skeletal formula
what are structural isomers?
compounds with the same molecular formula but different structural formula
how can the movement of functional groups create isomers?
in compounds containing a functional group, the functional group can be at different positions along the carbon chain
how can isomers have different functional groups?
sometimes 2 molecules containing different functional groups have the same molecular formula (e.g. aldehydes and ketones with the same number of carbon atoms)
what are the two ways that covalent bonds can be broken?
- homolytic fission
- heterolytic fission
what happens during homolytic fission?
- when a covalent bond breaks by homolytic fission, each of the bonded atoms takes one of the shared pairs of electrons from the bond
- each atom now has a single unpaired electron
what is a radical?
an atom or groups of atoms with an unpaired electron
what is heterolytic fission?
- when a covalent bond breaks by heterolytic fission, one of the bonded atoms takes both of the electrons from the bond
- the atom that takes both electrons becomes a negative ion
- the atom that doesn’t take electrons becomes a positive ion
what is the reaction mechanism?
information about how the reaction takes place
what are curly arrows used to show in reaction mechanisms?
the movement of electron pairs when bonds are being broken or made
what is an addition reaction?
in an addition reaction, two reactants join together to form one product
what is a substitution reaction?
an atom or groups of atoms is replaced by different atoms or groups of atoms
what is an elimination reaction?
the removal of a small molecule from a larger one
one reactant molecule forms two products