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    Chem Olympiad Imine-Carbonyl

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    Zest Ang Yi Yen
    The document provides an introduction to organic chemistry concepts including: 1. Nomenclature rules for naming organic compounds using prefixes, parent chains, locants, and suffixes. 2. Representations of functional groups such as alkanes, alkenes, alkynes, carboxylic acids, alcohols and others. 3. Details on specific functional groups including imine, nitrile, nitro, thiol, and sulphide groups and rules for naming compounds containing these groups.

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    Chem Olympiad Imine-Carbonyl

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    Zest Ang Yi Yen
    89 views55 pages
    The document provides an introduction to organic chemistry concepts including: 1. Nomenclature rules for naming organic compounds using prefixes, parent chains, locants, and suffixes. 2. Representations of functional groups such as alkanes, alkenes, alkynes, carboxylic acids, alcohols and others. 3. Details on specific functional groups including imine, nitrile, nitro, thiol, and sulphide groups and rules for naming compounds containing these groups.

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    The document provides an introduction to organic chemistry concepts including: 1. Nomenclature rules for naming organic compounds using prefixes, parent chains, locants, and suffixes. 2. Representations of functional groups such as alkanes, alkenes, alkynes, carboxylic acids, alcohols and others. 3. Details on specific functional groups including imine, nitrile, nitro, thiol, and sulphide groups and rules for naming compounds containing these groups.

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    Attribution Non-Commercial (BY-NC)
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    89 views55 pages

    Chem Olympiad Imine-Carbonyl

    Uploaded by

    Zest Ang Yi Yen
    The document provides an introduction to organic chemistry concepts including: 1. Nomenclature rules for naming organic compounds using prefixes, parent chains, locants, and suffixes. 2. Representations of functional groups such as alkanes, alkenes, alkynes, carboxylic acids, alcohols and others. 3. Details on specific functional groups including imine, nitrile, nitro, thiol, and sulphide groups and rules for naming compounds containing these groups.

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    of 55

    Introduction to Organic Chemistry

    Nomenclature
    Writing form: Prefix parent locant Suffix Steps: 1. Parent hydrocarbon 2. Number the atoms in main chain 3. Identify and number substituents 4. Write the name as a single word 5. (cycloalkane chair conformation)

    Number of C atoms 1 2 3 4 5 6 7 8 9 10

    Word root meth Eth Prop But Pent Hex Hept Oct Non Dec

    Functional Group Alkane Alkene Alkyne Carboxylic acid Alcohol

    Representation C-C single bond C-C double bond C-C triple bond -COOH -OH

    Nomenclature

    2, 3-dimethybutane

    Questions:
    1-bromo-1-chlorobutane

    2,2-dimethylpentane

    Cyclobutane

    1,1- dimethylcyclopentane

    1,4-dimethylcyclohexane

    Lines
    Bonds to atoms above the plane of the drawing (coming out, toward the viewer) are shown with a bold wedge ( ), with the narrow end of the wedge starting at the stereogenic center. Bonds to atoms below the plane (going in, away from the viewer) are shown with hash wedges ( ).

    Sawhorse representation and Newman projection


    Sawhorse representation
    Views C-C bond from an oblique angle
    Indicated spatial relationships by showing all the C-H bonds

    Newman Projection
    Views C-C bond directly end-on Carbon atoms are represented by a circle

    Available: http://image.wistatutor.com/content/hydrocarbons/newman-projections.gif

    Staggered and eclipsed


    Sawhorse projection

    Newman projection

    Stability

    Skeletal structures
    Propene

    Cyclohexane

    Benzene

    Benzene and phenyl


    The benzene ring All aromatic compounds are based on benzene, C6H6, which has a ring of six carbon atoms and has the symbol: Each corner of the hexagon has a carbon atom with a hydrogen attached.

    The phenyl group A hydrogen is removed from a benzene ring, C6H6. Like a methyl or an ethyl group, a phenyl group is always attached to something else (not carbon).

    Benzene-1,4-dicarboxylic acid

    2-hydroxybenzoic acid

    2,4,6-trichlorophenol

    Functional group
    A group of atoms whose bonding is the same from molecule to molecule. Imparts similar chemical and physical properties to the molecules which contain them.

    Imine Functional Group

    Also called Schiff Base =NH

    Imine
    Carbonnitrogen double bond Nitrogen attached to a hydrogen atom (H) or an organic group. The carbon has two additional single bonds

    Examples of Imines

    (E)-N-Benzylidenemethanamin

    Rhodopsin, an imine used in vision.

    Imines
    Related to ketones and aldehydes by replacement of the oxygen with an NR group When R = H, the compound is a primary imine When R is hydrocarbyl, the compound is a secondary imine

    R2C=NR'
    When R3 is OH, the imine is called an oxime

    When R3 is NH2 the imine is called a hydrazone

    Aldimines and ketimines


    A primary imine in which C is attached to both a hydrocarbyl and H is called a primary aldimine

    A secondary imine with such group is called a secondary aldimine

    A primary imine in which C is attached to two hydrocarbyls is called a primary ketimine

    A such group is called a secondary ketimine.

    Naming Imines
    Imines are systematically named by adding the word imine after the name of the corresponding aldehyde or ketone CH3CHNH ethanal imine (from ethanal, CH3CHO) Btw, is this a primary/secondary aldimine/ketamine?

    Naming Imines
    (CH3)2CNH Propanone imine Ethanal methyl imine CH3CHNCH3

    Nitrile
    CN

    Nitriles
    any organic compound that has a CN functional group Inorganic compounds containing the -CN group are not called nitriles, but cyanides

    Naming Nitriles
    2 ways of naming nitriles

    Cyano substituent style


    - The root name is based on the longest chain with the -CN as a substituent. - Chain is numbered so as to give the -CN group the lowest possible locant number - E.g. 1-cyanopropane

    Nitrile Style
    The nitrile suffix is used in a very similar manner to carboxylic acids Faced with same compound, CH3CH2CH2CN Functional group is a -CN, therefore suffix = nitrile Hydrocarbon structure is an alkane therefore Longest chain is C4 Butanenitrile

    Naming Nitriles (nitrile style)

    Benzonitrile

    Cyclopentanecarbonnitrile

    Naming Nitriles
    Butanedinitrile

    2-methyl-1-propanenitrile Bonus! How do you name this?

    Nitro Functional Group

    RNO2

    Nitro Functional Group


    O-N=O central nitrogen atom is involved in both a double bond and a single bond Highly explosive, various impurities or improper handling can easily trigger a violent exothermic decomposition (aka an explosion) An example is nitroglycerin

    Nitro R-NO2
    Aromatic nitro compounds. Trinitrotoluene (TNT) - A pale yellow, solid organic nitrogen compound used chiefly as an explosive, prepared by stepwise nitration of toluene

    Reactions: Reduction
    Nitro compounds are reduced to amines RNO2 + 3 H2 RNH2 + 2 H2O

    Naming Nitro Compounds


    Simply name the -NO2 as a nitro substituent

    Naming Nitro Compounds

    Nitromethane Guess how Nitrobenzene looks like?

    Thiol Functional Group

    Thiols
    Organosulfur compound that contains a carbon-bonded sulfhydryl (-C-SH or R-SH) group Have a foul smell Structurally similar to an alcohol but contains a sulfur atom in place of the oxygen atom normally found in an alcohol. Among the odorous principles in the scent of skunks and of freshly chopped onions

    Synthesis
    Reaction of related alcohol with hydrogen sulphide CH3OH + H2S CH3SH + H2O

    Naming Thiols
    Sulfur analogues of alcohols Named the same way too The root name is based on the longest chain with the -SH attached. The chain is numbered so as to give the thiol unit the lowest possible number. The thiol suffix is added after the hydrocarbon suffix : e.g. -ane + -thiol = -anethiol or -ene + thiol = -enethio

    Naming Thiols
    CH3CH(SH)CH3 Propan-2-thiol or 2-propanethiol

    1-Butanethiol

    Cyclopentanethiol

    Naming Thiols

    4-methylpentan-2-thiol

    Sulphide Functional Group


    Also known as Thioether

    Sulphides
    S atom bonded to two C atoms via s bonds R-S-R Named the same way as oxygen cousins, ethers Like many other sulfur-containing compounds, volatile thioethers characteristically have foul odors

    Naming Sulphides: "Simple" thioethers


    "Simple" thioethers If both groups are simple alkyl groups, then the thioether is usually named as alkyl alkyl thioether Alkyl groups are listed in alphabetical order If the two alkyl groups are the same, then it's a dialkyl thioether CH3-S-CH3 Dimethylsulphide CH3CH2SCH3 Ethyl Methyl

    Intermediate Thioethers
    If one of the groups is more complex then the thioether group is usually treated as an alkylthio- (i.e. R-S-) substituent. The more complex group (i.e. longer chain, more branched, other substituents) defines the root CH3CH2CH2SCH3
    1-methylthiopropane

    Complex Thioethers
    If both groups are complex then the ether can be named using thio E.g. CH3SCH2CH2CH3 Hydrocarbon structure is an alkane Functional group is an thioether, therefore prefix = -thio The longest continuous chain (including the S) is 5 therefore root = pent Numbering from the left as drawn to make the thio group locant 2 2-thiopentane

    Examples (Simple)

    Butyl ethyl sulphide

    Disulphides

    Disulphide bond
    Covalent bond, usually derived by the coupling of two thiol groups Also known as sulphide bridge

    Disulphide Bond
    Play an important role in the folding and stability of proteins E.g. two-amino-acid peptide cystine Composed of two cysteine amino acids joined by a disulfide bond

    Ever wondered why hair doesnt seem to decompose along with dead bodies?
    Over 90% of the dry weight of hair comprises proteins called keratins from the amino acid cysteine Hair has a high disulfide content The robustness conferred in part by disulfide linkages Recovery of virtually intact hair from ancient Egyptian tombs

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