Organic Chemistry - Lessons 1 & 2

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Questions and Answers

Which factor primarily contributes to the increase in melting and boiling points of larger hydrocarbons?

  • Increased hydrogen bonding
  • Reduced molecular weight
  • Stronger London forces (correct)
  • Higher dipole-dipole interactions

What is the primary characteristic of hydrocarbons that makes them generally non-polar?

  • Presence of multiple functional groups
  • Significant electronegativity difference
  • Equal sharing of electrons (correct)
  • Presence of hydroxyl groups

What defines a chiral carbon?

  • A carbon bonded to four different groups (correct)
  • A carbon that can rotate light to the left
  • A carbon bonded to two identical groups
  • A carbon that is part of a double bond

Which type of isomerism involves compounds with the same molecular formula but different structural formulas due to branching?

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

How are the prefixes for branches in a hydrocarbon's name typically formatted?

<p>Dashes separate numbers from letters (A)</p> Signup and view all the answers

What is the term used to describe the ability of an element to form long chains or cyclic structures?

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

Which of the following correctly describes a tetrahedral molecular geometry?

<p>4 electron pairs around the central atom (C)</p> Signup and view all the answers

What is the correct molecular formula for ethanol?

<p>C2H5OH (C)</p> Signup and view all the answers

According to the nomenclature of organic compounds, which prefix is used for a compound with three carbon atoms?

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

Which of the following is NOT a hydrocarbon derivative?

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

In a line diagram, what does the '−' symbol represent?

<p>A single bond (D)</p> Signup and view all the answers

What is the general formula for alkynes?

<p>$C_nH_{2n-2}$ (A)</p> Signup and view all the answers

Which molecular orbital hybridizes the 1s and 3p orbitals?

<p>sp3 (C)</p> Signup and view all the answers

What type of reaction do polar compounds like halo alkanes and alcohols undergo?

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

What characterizes the bonding in alkenes?

<p>A sigma bond and a pi bond (A)</p> Signup and view all the answers

Which type of isomerism involves the position of the double or triple bond in alkenes and alkynes?

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

What is the bond angle for sp3 hybridized alkanes?

<p>109.5° (D)</p> Signup and view all the answers

What reaction process do alkenes and alkynes typically undergo due to their pi electrons?

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

What type of reaction is characterized by the cleavage of bonds and production of radicals?

<p>Free radical substitution (C)</p> Signup and view all the answers

Which of the following statements is true regarding the solubility of alkanes?

<p>Alkanes are generally insoluble in polar solvents (D)</p> Signup and view all the answers

In naming a branched hydrocarbon, what does the prefix 'Di' signify?

<p>There are two separate branches (A)</p> Signup and view all the answers

When naming a hydrocarbon, which functional group takes priority if both hydroxyl (OH) and carboxylic acid (COOH) are present?

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

What type of reaction occurs when an electron-rich species replaces an atom or group in an aromatic compound?

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

Which of the following best describes a nucleophile?

<p>An electron-rich species (B)</p> Signup and view all the answers

What is the key characteristic of saturated organic compounds?

<p>They contain only single bonds (C)</p> Signup and view all the answers

Which of the following correctly identifies the process of combustion?

<p>Burning a compound in the presence of oxygen (C)</p> Signup and view all the answers

Which prefix is used to indicate that an isomer is optically active?

<p>L (-) (A), D (+) (B)</p> Signup and view all the answers

What is necessary for an addition reaction to occur in organic compounds?

<p>A double or triple bond (A)</p> Signup and view all the answers

What type of reaction occurs when an alcohol reacts with an alkyl halide to form an ether?

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

Which statement accurately describes ethers?

<p>They are good solvents and have low reactivity unless with strong acids. (A)</p> Signup and view all the answers

How are the alkyl groups in symmetrical ethers named?

<p>By naming one alkyl group and adding the prefix 'di'. (A)</p> Signup and view all the answers

What factor contributes to phenols being more acidic than alcohols?

<p>The oxygen atom is bonded to a sp-2 hybridized aromatic carbon. (D)</p> Signup and view all the answers

Which substituent characteristic makes the OH group in phenols a strong ortho/para directing group?

<p>It participates in resonance stabilization. (C)</p> Signup and view all the answers

What is the correct nomenclature of the ether CH3 - O - CH2 - CH2 - CH3?

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

What is a hazard associated with ethers due to their properties?

<p>They are easily absorbed through the skin and are poisonous. (A)</p> Signup and view all the answers

What type of chemical reaction is represented by 2CH3OH + 2Na → 2CH3O-Na + H2?

<p>Formation of alkoxides (C)</p> Signup and view all the answers

Which addition reaction is specifically characterized by the addition of H2O to an alkene?

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

What does Markovnikov’s Rule indicate about the addition of HBr to an alkene?

<p>The hydrogen will attach to the more substituted carbon atom. (B)</p> Signup and view all the answers

Which type of compound does not follow Huckel's rule?

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

In the context of aromatic compounds, which does the term 'ortho' refer to?

<p>Substituents that are adjacent to each other (C)</p> Signup and view all the answers

What is the general formula for cycloalkanes?

<p>C_nH_{2n} (A)</p> Signup and view all the answers

Which statement best describes electronegative substituents in aromatic compounds?

<p>They direct electrophiles to the meta position. (A)</p> Signup and view all the answers

Which formula accurately represents the general structure of alkyl halides?

<p>C_nH_{2n+1}X (A)</p> Signup and view all the answers

What effect does resonance have on the reactivity of aromatic compounds?

<p>It stabilizes them, making them less reactive. (A)</p> Signup and view all the answers

Which of these terms refers to the stable substitution pattern on aromatic compounds?

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

Flashcards

Isomers

Compounds with the same molecular formula but different structural arrangement.

Chiral Carbon

A carbon atom bonded to four different groups, making it asymmetric. It rotates the plane of polarized light.

Enantiomers

Stereoisomers that are non-superimposable mirror images of each other.

Cis-Trans Isomers

Isomers that differ in the arrangement of atoms around a double bond.

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Steric Hindrance

The larger the hydrocarbon chain, the weaker the intermolecular forces, leading to slower reactions.

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Substitution Reaction

A chemical reaction where an atom or group is replaced by another atom or group, typically occurring in saturated organic compounds with single bonds.

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Free Radical Substitution

A type of substitution reaction initiated by a free radical, which acts as the agent.

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Electrophilic Substitution

A substitution reaction where an electron-rich species replaces an atom or group, commonly seen in aromatic compounds with resonant structures.

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Nucleophilic Substitution

A substitution reaction where an electron-poor species replaces an atom or group.

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Addition Reaction

A chemical reaction where an atom or group is added to a compound, typically seen in unsaturated compounds with double or triple bonds.

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Electrophilic Addition

A type of addition reaction where an electron-poor species adds to a compound.

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Nucleophilic Addition

A type of addition reaction where an electron-rich species adds to a compound.

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Oxidation

A chemical reaction characterized by the addition of oxygen to an organic compound or the removal of hydrogen.

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Radical

A chemical species with an unpaired electron.

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Chain reaction

A reaction that proceeds in a series of steps, with each step involving a radical.

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Initiation

The initial step in a chain reaction where a radical is formed.

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Propagation

A step in a chain reaction where a radical reacts with a molecule to produce a new radical and a product.

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Termination

The final step in a chain reaction where radicals combine to form stable products.

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Catenation

The ability of an atom, especially carbon, to form long chains or ring structures by bonding with other atoms of the same element.

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Molecular Orbital

A region of space where electrons are shared by two or more atoms.

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Hybridized Molecular Orbital

A combination of atomic orbitals (primarily s and p) that results in a new hybrid orbital with different properties. This hybridization is essential for the geometry and bonding of molecules.

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Expanded Formula

A way to represent a molecule showing all atoms and bonds, useful for understanding the structure of the molecule.

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Line Diagram

A way to represent a molecule showing the arrangement of atoms and bonds, with each carbon atom represented by a vertex and each bond represented by a line.

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Homologous Series

A series of organic compounds with the same functional group but differing in length of the carbon chain by a -CH2 unit.

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Hydrocarbons

Organic compounds consisting only of carbon and hydrogen atoms.

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Alkanes

A group of hydrocarbons with single bonds between all carbon atoms. Their general formula is C(n)H(2n+2).

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Alcohol Dehydration Mechanism

A reaction where an alcohol's -OH group is removed or replaced with an atom or group, often through nucleophilic substitution or dehydration.

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Alcohol Reaction with Sodium

A reaction where an alcohol reacts with a strong base like sodium (Na) to produce an alkoxide ion and hydrogen gas.

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Ether Nomenclature

The naming of ethers follows IUPAC rules: name both alkyl groups connected to the oxygen atom, arrange them alphabetically. For symmetrical ethers, name the alkyl group and add 'di'. Non-IUPAC methods exist.

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Ethers

A class of organic compounds where the oxygen atom is bonded to two alkyl or aryl groups (R-O-R). They are relatively unreactive but can be good solvents. They are produced by reacting an alcohol with an alkyl halide.

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Phenols

Compounds with an -OH group directly attached to an aromatic ring. They are more acidic than alcohols due to the aromatic ring's influence.

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Electrophilic Aromatic Substitution in Phenols

A reaction where an electrophile substitutes a hydrogen atom on an aromatic ring. Phenols are particularly reactive in this type of reaction.

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Directing Effects of OH Group in Phenols

The OH group in phenols is a strong ortho/para directing group in electrophilic aromatic substitution reactions. This means that substituents will preferentially attach at the ortho or para positions relative to the OH group.

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Acidity of Phenols

Phenols are more acidic than alcohols due to the electron-withdrawing nature of the aromatic ring. This makes the hydrogen atom of the hydroxyl group more acidic.

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Hydrogenation

The addition of hydrogen gas (H2) to an alkene, breaking the double bond and forming a single bond. This results in an alkane.

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Hydration

The addition of water (H2O) to an alkene, breaking the double bond and forming an alcohol.

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Halogenation

The addition of a halogen (X2) to an alkene, breaking the double bond and forming a dihaloalkane.

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Hydrohalogenation

The addition of a hydrogen halide (HX) to an alkene, breaking the double bond and forming a haloalkane.

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Markovnikov's Rule

A rule stating that in the addition of a hydrogen halide (HX) to an alkene, the hydrogen atom attaches to the carbon with more hydrogen atoms already attached, while the halogen attaches to the carbon with fewer hydrogen atoms. This results in the formation of the more stable carbocation.

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Aromatic Compound

A cyclic compound with alternating double bonds and single bonds, fulfilling Huckel's rule (4n+2 pi electrons, where n is an integer) and exhibiting resonance stabilization.

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Electrophilic Aromatic Substitution

A substitution reaction where an electrophile attacks an aromatic compound, replacing a hydrogen atom with an electrophilic group.

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Cycloalkanes

Cyclic compounds without any double bonds.

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Study Notes

Organic Chemistry - Lesson 1

  • Catenation: The ability of carbon atoms to form long chains or rings/cyclic compounds.
  • Molecular Orbitals: The space where electrons are shared between two or more overlapping atomic orbitals.
  • Atomic Orbitals: S and P orbitals.
  • Hybridized Molecular Orbitals: A combination of S and P orbitals.
  • Molecular Orbitals (Examples):
    • sp³: 1s + 3p = 4 electron pairs, tetrahedral geometry
    • sp²: 1s + 2p + unhybridized p² = Ï€ bonds, trigonal planar geometry
    • sp: 1s + 1p + unhybridized pp² = 2Ï€ bonds, linear geometry

Organic Chemistry - Lesson 2

  • Homologous Series: A series of compounds with the same functional group, and successive members differ by a CHâ‚‚ group (14 mass units).

  • Hydrocarbons:

    • Alkanes: CnHâ‚‚n +2.
    • Alkenes: CnHâ‚‚n .
    • Alkynes: CnHâ‚‚n -2.
  • Hydrocarbon Derivatives:

    • Alcohols (-OH)
    • Carboxylic acids (-COOH)
    • Aldehydes (-CHO)
    • Ketones
    • Amines (-NHâ‚‚)
  • Physical Properties: Melting and boiling points increase as the molecular size of the hydrocarbon increases due to stronger London dispersion forces.

  • No dipole-dipole bonds: Hydrocarbon chains are nonpolar.

  • Steric hindrance: Increasing molecular size slows down reaction rates in the hydrocarbon due to steric hindrance.

Organic Chemistry - Lesson 3

  • Nomenclature:
    • Branch names first
    • Number branches by their place on the longest chain
    • Group branches alphabetically
  • Isomerism: Organic compounds with the same empirical/molecular formulas but different structural formulas.
  • Constitutional Isomers: Isomers that differ in the way atoms are arranged in the structure (branched vs. unbranched)
  • Stereoisomers: Isomers that differ in the spatial arrangement of atoms. Cis, trans, etc.

Organic Chemistry - Lesson 4

  • Alkanes: Saturated hydrocarbons (single bonds only).
  • Hybridization: sp³ with a bond angle of 109.5°.
  • Molecular Geometry: Tetrahedral.
  • Nomenclature: Greek root + -ane suffix for naming.
  • Chemical properties: Alkanes are generally nonpolar and insoluble in polar solvents (such as water).

Organic Chemistry -Lesson 5

  • Alkenes and Alkynes: Unsaturated hydrocarbons(double and triple bonds)
  • Alkenes: sp² hybridized. One sigma bond; one pi bond.
  • **Alkynes:**sp hybridized. One sigma bond, two pi bonds.
  • Isomers (examples):
    • Structural isomers (position / branch isomers)
    • Geometric isomers (cis/trans)

Organic Chemistry - Lesson 6

  • Aromatic Compounds: Compounds that obey Huckel's rule, with 4n + 2 pi electrons, (examples include benzene).
  • Benzene: 6 pi electrons, aromatic.
  • Aromatic Compounds are Stable: Stable due to resonance structures.
  • Huckel's Rule: All aromatic compounds must obey the Huckel rule with (4n+2) electrons.
  • Positional Isomerism examples: Ortho, para, meta- substituted benzene compounds.
  • Substitution Reactions (Aromatic): Replacing an atom or group in an aromatic compound.

Organic Chemistry - Lesson 7

  • Alkyl Halides: Organic compounds where a halogen (F, Cl, Br, or I) is bonded to an alkyl group.
  • Classification of Alkyl Halides (primary, secondary, tertiary) based on substitution patterns
    • Primary: One carbon bonded to the halogen
    • Secondary: Two carbons bonded to the halogen
    • Tertiary: Three carbons bonded to the halogen
  • Nomenclature: Using the root name plus -yl to indicate the halogen.

Organic Chemistry - Lesson 8

  • Alcohols: Organic compounds with an -OH or hydroxyl group.
  • Nomenclature: Prefix + Root + suffix + -ol.
  • Dehydration: Removal of water from a molecule typically using strong acids or phosphorus oxychloride (POCl3).

Organic Chemistry - Lesson 9

  • Ethers: Organic compounds with an oxygen atom bonded to two alkyl groups.

  • Nomenclature: Name alkyl groups alphabetically, separated by 'oxy', or 'di', for symmetrical ethers.

Organic Chemistry - Lesson 10

  • Phenols: Aromatic compounds with an -OH group bonded directly to an aromatic ring.
  • Reactivity and Substitution vs Alcohols: Phenols are more acidic than alcohols, and readily undergo electrophilic aromatic substitution reactions, but unlike alcohols are not alcohols with an aromatic ring..

Additional Concepts

  • Markovnikov's rule: Guide for predicting addition reactions to alkenes.
  • Leaving Groups: Atoms or groups that readily depart from a molecule. Good leaving groups are weak bases that easily leave (e.g., halogens or sulfonates).
  • SN1 Reactions: unimolecular nucleophilic substitution, Slow step is carbocation formation.
  • SN2 Reactions: bimolecular nucleophilic substitution. One step reaction, high steric hindrance.
  • E1 Reactions: elimination reactions follow SN1 mechanism.
  • E2 reactions: elimination reactions, follow SN2 mechanism. One step reaction.

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