FUNCHEM.11 Introduction to Organic Chemistry
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What distinguishes cis-but-2-ene from trans-but-2-ene?

  • The overall molecular weight
  • The number of carbons in the chain
  • The position of the double bond
  • The orientation of the substituents around the double bond (correct)
  • Which of the following statements is true regarding the boiling points of cis-but-2-ene and trans-but-2-ene?

  • Both have boiling points at the same temperature
  • Both are gases at room temperature
  • trans-but-2-ene has a higher boiling point than cis-but-2-ene
  • cis-but-2-ene has a higher boiling point than trans-but-2-ene (correct)
  • In terms of substituent arrangement, what characterizes cis isomers?

  • Substituents are on the same side of the double bond (correct)
  • Substituents are randomly distributed
  • Substituents are arranged alternately along the chain
  • Substituents are on opposite sides of the double bond
  • What is the molecular formula for both cis-but-2-ene and trans-but-2-ene?

    <p>C4H8 (A)</p> Signup and view all the answers

    What characteristic distinguishes organic compounds from inorganic compounds?

    <p>Presence of carbon atoms (C)</p> Signup and view all the answers

    What type of isomerism do cis-and trans-but-2-ene represent?

    <p>Geometric isomerism (A)</p> Signup and view all the answers

    Which bonding type is commonly found in organic compounds?

    <p>Covalent bonds (C)</p> Signup and view all the answers

    Which of the following is considered a functional group in organic chemistry?

    <p>Amine (A)</p> Signup and view all the answers

    Which of the following statements about aliphatic and aromatic hydrocarbons is true?

    <p>Aromatic hydrocarbons contain a benzene ring or similar structure. (A)</p> Signup and view all the answers

    What is the geometric feature of organic compounds as per valence bond theory?

    <p>Planar or tetrahedral arrangement (D)</p> Signup and view all the answers

    Which of the following about solubility of organic compounds is generally true?

    <p>They are usually poorly soluble in water. (D)</p> Signup and view all the answers

    What is an example of a structural isomer?

    <p>Different arrangement of carbon skeletons (B)</p> Signup and view all the answers

    Which element is most abundant in the compounds that form living matter?

    <p>Carbon (B)</p> Signup and view all the answers

    What are structural isomers?

    <p>Compounds with identical molecular formulas but different connectivity. (B)</p> Signup and view all the answers

    Which of the following statements about ethanol and dimethyl ether is correct?

    <p>Ethanol is soluble in all proportions, while dimethyl ether is slightly soluble. (C)</p> Signup and view all the answers

    What is the boiling point of dimethyl ether?

    <p>-23.6 °C (D)</p> Signup and view all the answers

    What characterizes geometric isomers?

    <p>They have different arrangements of atoms in space. (A)</p> Signup and view all the answers

    Which of the following is NOT a characteristic of structural isomers?

    <p>They have the same boiling points. (A)</p> Signup and view all the answers

    Which compound is a liquid at room temperature?

    <p>Ethanol (D)</p> Signup and view all the answers

    Which of the following statements is true for stereoisomers compared to structural isomers?

    <p>Stereoisomers have the same connectivity but differ in arrangement in space. (D)</p> Signup and view all the answers

    What is the melting point of ethanol?

    <p>-114.3 °C (B)</p> Signup and view all the answers

    What allows carbon to form long chains and cycles in organic compounds?

    <p>Its ability to share four valence electrons (D)</p> Signup and view all the answers

    How many covalent bonds can carbon form at maximum?

    <p>Four (C)</p> Signup and view all the answers

    What type of bond is formed by the head-on overlap of atomic orbitals?

    <p>Sigma (σ) bond (C)</p> Signup and view all the answers

    Which of the following statements is true regarding carbon's electronegativity?

    <p>Carbon is neither strongly electropositive nor strongly electronegative. (C)</p> Signup and view all the answers

    In which of the following compounds does carbon form a triple bond?

    <p>Ethyne (C2H2) (A)</p> Signup and view all the answers

    What describes the spatial orientation of the four C-H bonds in methane?

    <p>Tetrahedral arrangement (C)</p> Signup and view all the answers

    Which type of bond is characterized by sideways overlap of atomic orbitals?

    <p>Pi (π) bond (A)</p> Signup and view all the answers

    What is the lowest energy electron configuration for carbon?

    <p>1s2 2s2 2px1 2py1 (A)</p> Signup and view all the answers

    What does electronegativity determine in a covalent bond?

    <p>The polarization of bond (D)</p> Signup and view all the answers

    In Lewis structures, how are unshared valence electrons represented?

    <p>As dots (D)</p> Signup and view all the answers

    What symbol represents a triple bond in line structures?

    <p>Three lines (D)</p> Signup and view all the answers

    Which of the following statements about hydrocarbons is true?

    <p>They can be aromatic or aliphatic. (C)</p> Signup and view all the answers

    What defines a functional group in organic chemistry?

    <p>A distinct set of physical properties (B)</p> Signup and view all the answers

    In a line structure, what does an intersection of two lines typically represent?

    <p>A CH2 group (C)</p> Signup and view all the answers

    How are lone pairs shown in Lewis structures?

    <p>Expressed as pairs of dots (C)</p> Signup and view all the answers

    Which element has a similar electronegativity value to carbon?

    <p>Hydrogen (B)</p> Signup and view all the answers

    Which type of hydrocarbon does NOT include aromatic compounds?

    <p>Aliphatic hydrocarbons (C)</p> Signup and view all the answers

    What represents the bonding characteristics between atoms in line structures?

    <p>The type of line used (D)</p> Signup and view all the answers

    Which functional group is characterized by a carbon-oxygen double bond and contains a hydrogen atom attached to the carbon?

    <p>Aldehyde (C)</p> Signup and view all the answers

    Which family name describes a compound containing only C-H and C-C bonds?

    <p>Alkane (C)</p> Signup and view all the answers

    Which of the following is a trait of carbonyl functional groups?

    <p>They contain a polarized covalent carbon-oxygen double bond. (A)</p> Signup and view all the answers

    Which of these options correctly describes a thiol?

    <p>A sulfur-containing organic compound with the structure R-SH. (D)</p> Signup and view all the answers

    What defines an aromatic hydrocarbon?

    <p>It has a cyclic structure with alternating double bonds. (D)</p> Signup and view all the answers

    Which functional group is represented by the formula R-C(=O)-OH?

    <p>Carboxylic acid (C)</p> Signup and view all the answers

    Which of the following is NOT a classification of carbonyl compounds?

    <p>Ether (B)</p> Signup and view all the answers

    What distinguishes a nitrile from other functional groups?

    <p>It contains a carbon-nitrogen triple bond. (C)</p> Signup and view all the answers

    Which functional group is indicated by R-S-R'?

    <p>Sulfide (C)</p> Signup and view all the answers

    Which of the following compounds is an example of an alkyne?

    <p>Ethyne (A)</p> Signup and view all the answers

    Which functional group has a structure that typically contains two carbon atoms bonded to an oxygen atom by a double bond on one end and a hydroxyl group on the other?

    <p>Carboxylic acid (A)</p> Signup and view all the answers

    What is the general formula for alcohols?

    <p>R-OH (C)</p> Signup and view all the answers

    What is the primary feature of aromatic compounds?

    <p>They exhibit resonance due to their cyclic structures. (A)</p> Signup and view all the answers

    Flashcards

    Organic Chemistry

    The study of the structures, properties and syntheses of compounds containing carbon.

    Organic Compounds

    Compounds consisting of carbon atoms bonded to each other and other non-metal atoms like H, O, N, S, and halogens.

    Inorganic Compounds

    Compounds that do not contain carbon, except for carbonates, bicarbonates, and cyanides.

    Carbon's Chain Forming Ability

    The ability of carbon to form long chains and rings with other carbon atoms, creating diverse structures.

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    Carbon's Bonding with H, N, O

    Carbon can bond with hydrogen, nitrogen, and oxygen, forming the basis of most living organisms.

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    Carbon's Bond Variety

    Carbon can form single, double, or triple bonds, leading to a huge variety of 3D structures.

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    Covalent Bonding

    Organic compounds are often held together by covalent bonds, sharing electrons between atoms.

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    Ionic Bonding

    Inorganic compounds typically have ionic bonds, where one atom gives an electron to another.

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    Why carbon is vital for organic chemistry?

    Carbon is a group 4 element, meaning it has 4 valence electrons. These electrons can be shared, forming 4 strong covalent bonds with other carbon atoms or heteroatoms. This allows for the formation of long chains and cycles, making carbon the backbone of organic compounds.

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    Why silicon is not as important for organic chemistry as carbon?

    Although silicon is also a group 4 element and can form 4 covalent bonds, it's less suitable for complex organic structures. This is due to its larger size, weaker bonds, and lower stability when forming long chains.

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    What holds organic molecules together?

    Covalent bonds in organic compounds are formed by the sharing of electrons between atoms. These bonds are strong and crucial for holding the molecule together.

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    What is a sigma bond?

    A sigma bond is a covalent bond formed by the direct head-on overlap of atomic orbitals. This type of bond is strong and holds the atoms closely together. All single bonds between carbon atoms are sigma bonds.

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    What is a pi bond?

    A pi bond is a covalent bond formed by the sideways overlap of atomic orbitals. This type of bond is weaker than a sigma bond and occurs in addition to a sigma bond, creating double or triple bonds. Pi bonds are responsible for the planar structure of molecules like ethene.

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    Describe the bonding in methane (CH4).

    Methane (CH4) has four single bonds between carbon and hydrogen atoms. Each C-H bond is a sigma bond, formed by head-on overlap of orbitals. These four bonds are oriented in a tetrahedral shape, resulting in a 109.5° bond angle.

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    Describe the bonding in ethene (CH2CH2).

    Ethene (CH2CH2) has a double bond between two carbon atoms, composed of one sigma bond and one pi bond. This double bond restricts rotation around the carbon-carbon axis, making the molecule planar.

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    Describe the bonding in ethyne (CHCH).

    Ethyne (CHCH) has a triple bond between two carbon atoms, composed of one sigma bond and two pi bonds. The two pi bonds significantly shorten the carbon-carbon distance and make the molecule linear.

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    Electronegativity

    The ability of an atom to attract electrons towards itself in a covalent bond.

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    Polar Covalent Bond

    A covalent bond where electron sharing is unequal due to a difference in electronegativity between the atoms.

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    Lewis Structure

    A visual representation of a molecule showing all valence electrons as dots and lines representing covalent bonds.

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    Line Structure

    A simplified representation of organic molecules, where carbon and hydrogen atoms are implied by lines and intersections.

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    Functional Group

    A group of atoms within a molecule that is responsible for its characteristic chemical properties.

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    Hydrocarbon

    A compound that contains only carbon and hydrogen atoms.

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    Aliphatic Hydrocarbon

    Any non-aromatic hydrocarbon, characterized by open chains or branched structures.

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    Dashed Bond

    A covalent bond that points away from the viewer in a 3D representation of a molecule.

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    Wedge Bond

    A covalent bond that points towards the viewer in a 3D representation of a molecule.

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    Lone Pair

    A pair of electrons that are not involved in bonding and reside on an atom.

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    Geometric Isomers

    Isomers that have the same molecular formula but differ in the spatial arrangement of their atoms due to restricted rotation around a double bond.

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    Cis Isomers

    Geometric isomers where the substituents are on the same side of the double bond.

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    Trans Isomers

    Geometric isomers where the substituents are on opposite sides of the double bond.

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    Boiling Point Differences

    The difference in boiling point between cis and trans isomers is attributed to the dipole moment.

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    Why Carbon is the Backbone of Organic Chemistry?

    A carbon atom has 4 valence electrons, allowing it to form 4 covalent bonds with other atoms, leading to long chains and complex structures.

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    What are structural isomers?

    Structural isomers have the same molecular formula but different arrangements of atoms, resulting in different physical and chemical properties.

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    What are geometric isomers?

    Geometric isomers have atoms attached in the same order but differ in their spatial arrangement. Importantly, they are not mirror images of each other.

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    How do ethanol and dimethyl ether differ?

    Ethanol (CH3CH2OH) is a liquid at room temperature and is soluble in water, while dimethyl ether (CH3OCH3) is a gas and less soluble in water. This difference arises from the unique arrangement of atoms in each molecule, affecting bonding and properties.

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    What are stereoisomers?

    The term 'stereoisomers' refers to molecules that have the same molecular formula and the same sequence of atoms but differ in their arrangement in 3-dimensional space.

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    What are diastereomers?

    Diastereomers are a type of stereoisomer where the molecules are not mirror images of each other. This means they have different spatial arrangements but are not enantiomers.

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    What are enantiomers?

    Enantiomers are a type of stereoisomer where the molecules are non-superimposable mirror images of each other. They have the same connectivity but different configurations in 3D space.

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    What is chirality?

    Chirality is a property of molecules that have a non-superimposable mirror image. It arises from the presence of a chiral center, which is an atom with four different substituents.

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    What is a chiral center?

    A chiral center is an atom in a molecule that is bonded to four different groups. This asymmetry leads to chirality, meaning the molecule has two non-superimposable mirror image forms.

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    What is an aromatic hydrocarbon?

    A type of hydrocarbon with a specific ring structure. This ring is highly stable and exhibits unique chemical properties.

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    What is an alkane?

    An alkanes is a hydrocarbon that contains only single bonds between carbon atoms.

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    What is an alkene?

    An alkene is a hydrocarbon that contains at least one double bond between carbon atoms.

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    What is an alkyne?

    An alkyne is a hydrocarbon that contains at least one triple bond between carbon atoms.

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    What are functional groups?

    Groups of atoms within a molecule that are responsible for the molecule's characteristic chemical properties.

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    What is a hydrocarbon?

    Molecules containing only carbon and hydrogen atoms and no other elements. Alkanes, alkenes and alkynes are all examples of hydrocarbons.

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    What is an alcohol?

    A class of organic compound characterized by the presence of a hydroxyl group (-OH) attached to a carbon atom.

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    What is an ether?

    A class of organic compound characterized by the presence of an ether group (-O-) linking two alkyl groups.

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    What is a thiol?

    A class of organic compound characterized by the presence of a thiol group (-SH) attached to a carbon atom.

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    What is an amine?

    A class of organic compound characterized by the presence of an amine group (-NH2) attached to a carbon atom.

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    What is a nitrile?

    A class of organic compound characterized by the presence of a nitrile group (-CN) attached to a carbon atom.

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    What is a halide?

    A class of organic compound characterized by the presence of a halide group (-X) attached to a carbon atom. (Where X is chlorine, bromine or iodine)

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    What is a carbonyl group?

    The most important functional group in organic chemistry, characterized by a carbon atom double-bonded to an oxygen atom.

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    What is an aldehyde?

    A class of organic compound characterized by the presence of a carbonyl group (C=O) where the carbon atom is bonded to one hydrogen atom and one alkyl group.

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    What is a ketone?

    A class of organic compound characterized by the presence of a carbonyl group (C=O) where the carbon atom is bonded to two alkyl groups.

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    Study Notes

    Fundamentals of Medical and Pharmaceutical Chemistry

    • This lecture series covers FUNCHEM.11, an introduction to organic chemistry.
    • The lecturer is Dr. Declan Gaynor.

    Learning Outcomes

    • Compare properties of organic and inorganic compounds.
    • Identify and describe structural geometry and bonding in organic compounds using valence bond theory.
    • Interpret and construct Lewis structures, condensed structures and line structures of organic compounds.
    • Identify and describe functional groups (alkane, alkene, alkyne, alcohol, thiol, ether, sulphide, aldehyde, ketone, carboxylic acid, amine, amide, ester, halide, acid halide, aromatic).
    • Identify aliphatic and aromatic hydrocarbons.
    • Describe and identify examples of structural, geometric, and optical isomers.

    Understanding Organic Chemistry

    • Organic chemistry is crucial as the enzyme HMG-CoA reductase is vital in cholesterol synthesis.
    • Atorvastatin (Lipitor) is a key example of a drug that works by targeting this enzyme.

    Introduction to Organic Chemistry

    • Organic chemistry is the chemistry of carbon compounds.
    • Carbon compounds provide constituents for living matter including DNA, proteins, and carbohydrates, and produce energy through conversion to CO2.
    • Carbon is less than 1% of the earth's crust, but it forms chains of atoms (linear, branched, cyclic), bonds with elements such as H, N, O (making up 98% of living tissue), and has many 3-dimensional structures.

    Basic Components in Organic Chemistry

    • Organic compounds are formed by carbon atoms covalently bonded to each other and other non-metal atoms like H, O, N, S, and halogens.
    • All other compounds are inorganic compounds

    Organic vs Inorganic Compounds

    • Organic chemistry studies the structure, properties, and synthesis of organic compounds.
    • Organic molecules have covalent bonds, are often poorly soluble in water, and have relatively low melting and boiling points, in contrast to inorganic molecules which have ionic bonds, are generally highly soluble in water, and have high melting and boiling points.

    Why Carbon?

    • Carbon is a group 4 element that can share four valence electrons, enabling the formation of four strong covalent bonds with other carbon atoms and other heteroatoms (elements other than carbon and hydrogen).
    • Unlike silicon, which is also in group 4, carbon can form long chains and cycles.

    Carbon Summary

    • Carbon has an atomic number of 6, with 6 electrons arranged in shells and orbitals (1s² 2s² 2p⁴).
    • Carbon has four valence electrons.
    • Carbon forms strong bonds with neighboring carbon atoms.
    • Carbon's electronegativity value is 2.5, making it neither strongly electropositive nor electronegative

    Covalent Bonding

    • Covalent bonds in organic compounds result from electron sharing.
    • Organic chemistry uses the term "bond" to describe a shared pair of electrons, with four valence electrons for carbon and enabling a maximum of four covalent bonds.
    • The bonds are represented by lines between atomic symbols to represent shared electron pairs.
    • There are single, double and triple bonds. (Simple examples showing methane, ethene, and ethyne are provided).
    • A sigma (σ) bond forms by head-on overlap of atomic orbitals.
    • A pi (π) bond forms by sideways overlap of atomic orbitals (describing sigma and pi bonds in the scenarios of ethene and ethyne).

    3D Shape of Organic Compounds

    • Methane's tetrahedral geometry shows all four C-H bonds are identical and spatially oriented.
    • C-H bond lengths and angles (109.5°) are also presented.
    • Geometric features of ethene and ethyne are also described.

    Polar Covalent Bonds

    • Electronegativity increases from left to right within a row and decreases from top to bottom of a row within the periodic table.
    • The difference in electronegativity between atoms influences bond polarity (unequal electron sharing), with larger differences leading to more ionic character.
    • Biologically relevant examples are illustrated.

    Lewis Structures

    • In Lewis structures, all valence electrons are represented.
    • Covalent bonds (single, double, triple) are depicted as lines between atoms.
    • Unshared valence electrons are shown as dots on the respective atom(s).
    • Examples are provided. (Methylamine and methanol)

    Line Structures

    • Line structures are a more convenient way to depict organic compound connectivity, with lines representing carbon chains and intersections representing other elements or functional groups.
    • End of lines represent CH₃(methyl) while double lines represent C=C and triple lines represent C≡C.

    Organic Molecule Categories

    • Organic compounds contain carbon and other elements (hydrogen, oxygen, nitrogen, sulphur and halogens).
    • Functional groups are specific atoms or groups of atoms that cause certain characteristic physical and chemical properties.
    • Hydrocarbon examples are provided: aliphatic and aromatic.

    Classification of Organic Compounds

    • Functional groups have distinct characteristics.
    • Simple examples of alkane (ethane), alkene (ethene), alkyne (ethyne), and aromatic (benzene) functional groups are provided.

    Functional Groups (Alcohols, Ethers, Thiols, Sulfides)

    • Several functional group families: alcohol, ether, thiol, and sulfide are described along with examples in terms of structure and simple examples.

    Functional Groups (Amines, Nitriles, Halides, Trifluoromethyls)

    • Descriptions and simple examples of amine, nitrile, halide, and trifluoromethyl functional groups and their structures.

    Carbonyl Functional Groups

    • Carbonyl functional groups are important polar covalent groups in organic chemistry based on a carbon-oxygen double bond.

    Functional Groups: Carbonyl (Aldehydes, Ketones, Carboxylic Acids, Esters)

    • Families like aldehyde, ketone, carboxylic acid, and ester are presented with their structures and simple examples.

    Functional Groups: Carbonyl (Amides, Acyl Halides, Carboxylic Anhydrides, Esters of Phosphoric Acid)

    • Further carbonyl functional group types: Amide, acyl halide, carboxylic acid anhydride, ester of phosphoric acid are included, and their associated structures.

    Structural Isomers

    • Structural isomers have the same molecular formula but different structural formulas (different connectivity).
    • These isomers can have different physical and biological properties given different structural arrangements. Examples provided include ethanol and dimethyl ether.

    Stereoisomers: Geometric Isomers

    • Geometric isomers (diastereomers) have the same order of atom attachment but different arrangements in space (not mirror images of one another).
    • Examples include cis-but-2-ene and trans-but-2-ene.

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    Description

    This quiz covers the fundamentals of medical and pharmaceutical chemistry with a focus on organic compounds. It explores the properties, structures, and functional groups of various organic compounds, alongside important concepts in bonding and isomerism. Designed to enhance understanding in the field of organic chemistry, it's essential for students in this discipline.

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