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Intro to organic chemistry ( orgo ). SCH4U – Unit B. Organic Compounds. Organic chemistry: chemistry of carbon compounds Exceptions are oxides of carbon (CO 2 and CO), carbonates, bicarbonates, and cyanides Carbon atoms are generally bonded to: Each other Hydrogen atoms

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organic compounds
Organic Compounds
  • Organic chemistry: chemistry of carbon compounds
    • Exceptions are oxides of carbon (CO2 and CO), carbonates, bicarbonates, and cyanides
  • Carbon atoms are generally bonded to:
    • Each other
    • Hydrogen atoms
    • Other specific elements (O, N, S, P and others)
why study organic chemistry
Why study organic chemistry?
  • Life is carbon-based. Everyone is made up of organic compounds. There are more known carbon compounds than any other element.
  • There are several million known organic compounds with ~30,000 more being “discovered” each year.
  • Some common organic compounds include plastics, synthetic and natural fibres, dyes, drugs, pesticides, lighter fluid, and gasoline.
the carbon atom
The carbon atom
  • Carbon has four valence electrons allowing it to form four bonds with other atoms by sharing its electrons
    • This results in a tetrahedral shape
  • Carbon forms covalent bonds (sharing of electrons) with carbon atoms
classification
Classification
  • Since organic compounds are composed almost entirely of carbon, they are sometimes referred to as hydrocarbons
  • Hydrocarbons can be divided into:
    • Aliphatics: carbon atoms in an open chain structure; may have branches, but no rings
    • Alicyclics: carbon atoms arranged in a ring structure
    • Aromatics: structures related to benzene (C6H6)
classification1
Classification
  • Aliphatics can be further categorized into:
    • Alkanes: contains only single bonds (saturated)
    • Alkenes: contains at least one double bond (unsaturated)
    • Alkynes: contains at least on triple bond
diagrams formulas
Diagrams & formulas
  • A number of different (but related) diagrams used to express structures in organic chemistry:
    • Empirical molecular formula
    • Expanded molecular formula
    • Complete structural formula
    • Condensed structural formula
    • Line structural formula
    • 3D structural formula
alkanes1
Alkanes
  • Only single bonds present in the main chain
  • General formula is CnH2n+2
  • Form a tetrahedral shape
    • Note: more on shapes in the next unit
  • Create a 109.5° angle between bonds
  • Considered “saturated” because no other hydrogen atoms can be added
  • Always end in “~ane”
nomenclature
Nomenclature
  • Three parts to organic chemistry nomenclature:
    • Prefix: indicates number, type and location of branches and/or functional groups (if any)
    • Root: indicates the number of carbon atoms in the main (parent) chain
    • Suffix: indicates the number and location of double or triple bonds (if any) and/or highest priority functional group
let s draw alkanes
Let’s draw alkanes!
  • Draw all ten basic alkanes and name them.
alkyl groups and branching
Alkyl groups and branching
  • Each branch of a hydrocarbon is referred to as an alkyl group (if it contains only C and H)
  • Alkyl groups use the same basic roots as alkanes
  • Alkyls always end in “~yl”
  • Also contain a number and hyphen in front to indicate location on the main carbon chain
    • Example: 2-methyl pentane
alkyl groups and branching1
Alkyl groups and branching
  • Find the longest carbon chain and assign sequential numbers to each carbon
    • Assign these numbers temporarily starting from both ends of the carbon chain
    • Ultimately will select only one set of numbers to use
  • The goal is to use the numbering along the carbon chain that gives the lowest values assigned to branches
alkyl groups and branching2
Alkyl groups and branching
  • Let’s try some! Draw 3-ethyl octane…
alkyl groups and branching4
Alkyl groups and branching
  • When there is more than one branch, they are listed in front of the root and suffix according to alphabetical order of the name of the alkyl group
  • Try naming…
  • 4-ethyl 3-methyl heptane
alkyl groups and branching5
Alkyl groups and branching
  • If there is more than one of any given alkyl group
    • Indicate all the number for the positions using commas to separate the numbers, and
    • Use prefixes (on the prefixes – confused yet?) to indicate the number present
alkyl groups and branching6
Alkyl groups and branching
  • Try naming…
  • 5,6-diethyl-3,3,4-trimethyl nonane
alkenes
Alkenes
  • At least one double bond present in the main chain
  • General formula is CnH2n
  • Form a trigonal planar shape
    • Note: more on shapes in the next unit
  • Create a 120° angle between bonds
  • Considered “unsaturated” because other hydrogen atoms can be added
  • Always end in “~ene”
nomenclature1
Nomenclature
  • Identify and name the longest carbon chain that CONTAINS THE DOUBLE BOND(S).
  • Number the carbons in the chain so that the two carbons involved in the double bond have the lowest possible numbers.
    • If the double bond is equidistant from both ends, number the chain so that the substituent(s) have the lowest possibly number.
  • Follow same rules for identifying and naming prefixes.
nomenclature2
Nomenclature
  • Try naming this…
  • 2-ethyl 1-pentene
nomenclature3
Nomenclature
  • Now let’s draw 1-butene and 2-butene…

1-butene 2-butene

nomenclature4
Nomenclature
  • Let’s try a structure with more than one double bond…

1,3-pentadiene

nomenclature5
Nomenclature
  • Let’s put everything together and name…
  • 4-ethyl-3,6-dimethyl 1,2,4-octatriene
diastereomers
Diastereomers
  • Consider the following compounds…

cis-2-butene trans-2-butene 2-methyl-

1-propene

diastereomers1
Diastereomers
  • Not superimposable upon one another
  • Result from lack of free rotation around the double bond
  • Priorities are assigned to the two groups attached to the carbon atoms on either side of the double bond (starting with the carbon to the left of the double bond) based on atomic number
    • Largest atomic number at the first point of difference has the highest priority
diastereomers2
Diastereomers
  • If two highest priority groups are on the same side of the double bond (top or bottom)…
    • cis configuration
  • If two highest priority groups are on the opposite side of the double bond…
    • trans configuration
alkynes
Alkynes
  • At least one triple bond present in the main chain
  • General formula is CnH2n-2
  • Form a linear shape
    • Note: more on shapes in the next unit
  • Create a 180° angle between bonds
  • Considered “unsaturated” because other hydrogen atoms can be added
  • Always end in “~yne”
nomenclature6
Nomenclature
  • Identify and name the longest carbon chain that CONTAINS THE TRIPLE BOND(S).
  • Number the carbons in the chain so that the two carbons involved in the triple bond have the lowest possible numbers.
    • If the triple bond is equidistant from both ends, number the chain so that the substituent(s) have the lowest possibly number.
  • Follow same rules for identifying and naming prefixes.
nomenclature7
Nomenclature
  • Try naming this…
  • 3,4-dimethyl 1-hexyne
nomenclature8
Nomenclature
  • Now let’s draw 1-butyne and 2-butyne…

1-butyne 2-butene

nomenclature9
Nomenclature
  • Let’s try a structure with more than one triple bond…

2,4-hexadiyne

nomenclature10
Nomenclature
  • Let’s put everything together and name…
  • 4-ethyl-4,5-dimethyl 2,6-octadiyne
alicyclics
Alicyclics
  • Connected end-to-end forming a ring
  • Have single and/or double bonds present in the main chain
  • General formula is CnH2n
  • Can be “saturated” or “unsaturated”
  • Suffix changes depending on presence of double bonds
  • Prefix used is always “cyclo~” before the root
nomenclature11
Nomenclature
  • Try naming…

cyclobutane cyclo-1-pentene

cyclopent-1-ene

nomenclature12
Nomenclature
  • Try drawing…

cyclo-1,4-hexadiene 2,7-diethyl-4-methyl

cyclo-1,3,5-heptatriene

aromatics
Aromatics
  • Based on benzene and the presence of benzene-like rings
  • Benzene is a six-carbon ring with three double bonds
    • Cyclo-1,3,5-hexatriene
  • However, the electrons in the double bonds are actually spread over the whole molecule = delocalized
    • Benzene actually has six identical “1 ½” bonds
aromatics1
Aromatics
  • Creates greater stability in the molecule
  • These “1 ½” bonds do not behave/react like double bonds
  • Molecules that have this type of sharing are referred to as aromatic compounds

Benzene

aromatics2
Aromatics
  • Some common aromatics…

benzene napthalene

antracene

nomenclature13
Nomenclature
  • Number carbons in benzene ring assigning lowest number to a branch.
    • If more than one branch exists, start numbering at the branch that contains the group with the highest priority (most complex).
  • Name branches attached to the benzene ring, assigning numbers to each branch.
    • If only one branch is present, a number does not need to be assigned.
  • Branches are placed before the root as a prefix.
nomenclature14
Nomenclature
  • Priority of branches on benzene…
nomenclature15
Nomenclature
  • When benzene has only two branches, position numbers do not have to be used
  • Instead, prefixes ortho-, meta-, and para- replace position numbers

1,2-dimethyl benzene

ortho-dimethyl benzene

nomenclature16
Nomenclature

1,3-dimethyl benzene 1,4-dimethyl benzene

meta-dimethyl benzene para-dimethyl benzene

nomenclature17
Nomenclature
  • IUPAC has retained many of the common names for aromatics…
nomenclature18
Nomenclature
  • Let’s try naming…

3-ethyl-5-methyl phenol

nomenclature19
Nomenclature
  • Let’s try drawing…

2,6-diethyl-3-methyl benzaldehyde

nomenclature20
Nomenclature
  • For use when:
    • Naming compounds with >1 fxn’l group
    • Naming compounds with a complicated substituent
nomenclature21
Nomenclature
  • Try naming…

3-phenyl hexane

nomenclature22
Nomenclature
  • Try drawing…

4,6-diphenyl 2-octene

up next
Up next
  • That covers the basics of hydrocarbons in organic chemistry.
  • Next we will cover functional groups!