Organic Chemistry: Alkanes and Reactions
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Questions and Answers

Which of the following alkanes would have the highest boiling point?

  • CH3CH2CH2CH2CH3 (correct)
  • CH3CH2CH3
  • CH3CH2CH2CH3
  • CH3CH(CH3)CH2CH3

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

  • Volatility is not affected by branching.
  • Volatility increases with increasing molecular size.
  • Volatility is not affected by molecular size.
  • Volatility decreases with increasing branching. (correct)

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

  • Density is not affected by molecular size.
  • Density is not affected by branching.
  • Density increases with increasing branching.
  • Density decreases with increasing molecular size. (correct)

Which of the following alkanes would be the most volatile?

<p>CH3C(CH3)2CH3 (D)</p> Signup and view all the answers

What products are formed in heterolytic cleavage?

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

Which of the following is a characteristic of homolytic cleavage?

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

In the halogenation of methane, what is required for the reaction to occur?

<p>Sunlight or UV light (D)</p> Signup and view all the answers

What type of species are formed when $CH_3Br$ undergoes heterolytic fission?

<p>$CH_3^+$ and $Br^-$ (D)</p> Signup and view all the answers

What happens to the electron pair in the carbon-bromine bond during homolytic fission?

<p>One electron is transferred the carbon atom, the other to the bromine atom. (A)</p> Signup and view all the answers

What is the correct order for naming substituents in an organic compound?

<p>Inorganic substituents first, then organic substituents (A)</p> Signup and view all the answers

Which of the following is an example of an inorganic substituent?

<p>NO2- (nitro) (D)</p> Signup and view all the answers

How should the position of a substituent be indicated in an organic compound?

<p>With the smallest possible number (B)</p> Signup and view all the answers

What is the correct IUPAC name for the condensed structure CH3Cl?

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

Which prefix should be used to indicate two identical substituents?

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

What is hybridization in the context of atomic orbitals?

<p>The combination of two or more atomic orbitals to form new hybrid orbitals. (A)</p> Signup and view all the answers

Why does carbon exhibit a covalency of four despite having only two unpaired electrons?

<p>Hybridization allows a 2s electron to be promoted to a 2p orbital. (B)</p> Signup and view all the answers

What type of reactions do alkanes predominantly undergo?

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

What type of bond is formed between carbon atoms in pure alkanes?

<p>Sigma bonds that can rotate freely. (D)</p> Signup and view all the answers

Why do alkanes have low reactivity?

<p>They lack any double or triple bonds. (B)</p> Signup and view all the answers

In tetrachloromethane (CCl4), how many equivalent carbon-chlorine bonds are formed?

<p>Four equivalent bonds are formed through hybridized orbitals. (D)</p> Signup and view all the answers

In the reaction CH₄ + Cl₂ → CH₃Cl + HCl, what type of reaction is taking place?

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

What is the effect of hybridization on the energy of the orbitals involved in bond formation?

<p>Hybridization lowers the energy of the new hybrid orbitals. (B)</p> Signup and view all the answers

Which hydrocarbon has a lower boiling point based on size and volatility?

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

Which of the following statements about the bonds in alkanes is true?

<p>C-H and C-C bonds are nonpolar. (D)</p> Signup and view all the answers

Which type of solvents can alkanes dissolve in?

<p>Non-polar organic solvents (B)</p> Signup and view all the answers

What is the physical state of C₁₉ and above alkanes at room temperature?

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

Why are alkanes insoluble in water?

<p>Hydration energy is insufficient to overcome alkane's intermolecular forces. (A)</p> Signup and view all the answers

Which of the following statements about the color of alkanes is true?

<p>Alkanes are colorless in their pure state. (B)</p> Signup and view all the answers

In the halogenation of methane, what occurs during the initiation step?

<p>A chlorine molecule breaks down into two chlorine free radicals. (B)</p> Signup and view all the answers

What products are formed when a chlorine free radical ($Cl$) abstracts a hydrogen atom from methane ($CH_4$) during the propagation step?

<p>$CH_3$ and $HCl$ (C)</p> Signup and view all the answers

Which of the following correctly describes the role of free radicals in the halogenation of alkanes?

<p>Free radicals initiate and propagate the chain reaction by continuously generating new reactive species. (A)</p> Signup and view all the answers

In the termination step of methane halogenation, which of the following reactions leads to the formation of ethane?

<p>$CH_3 + CH_3 → C_2H_6$ (C)</p> Signup and view all the answers

When methane is in excess during halogenation, what is the major product formed?

<p>Chloromethane ($CH_3Cl$) (C)</p> Signup and view all the answers

What characterizes an addition reaction?

<p>Only one molecule is formed from the reactants. (A), Reactants must contain an unsaturated bond. (D)</p> Signup and view all the answers

Which of the following best describes an elimination reaction?

<p>It results in the formation of multiple bonds while losing atoms. (D)</p> Signup and view all the answers

What is the primary result of hydrogenation in organic reactions?

<p>It adds hydrogen molecules to an unsaturated compound. (A)</p> Signup and view all the answers

Which reaction process involves the removal of water from a species?

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

What common chemical process occurs during saponification?

<p>Formation of soap and glycerol from a fat. (C)</p> Signup and view all the answers

What is the IUPAC name of the compound $CH_3CH(CH_3)CH(Cl)CH(CH_3)CH_2CH_3$?

<p>3-chloro-2,4-dimethylhexane (B)</p> Signup and view all the answers

What is the correct IUPAC name for the compound $ClCH_2CH_2CH_3$?

<p>4-chloro-1-ethylpentane (B)</p> Signup and view all the answers

What is the IUPAC name of the compound $(CH_3)_2CH(CH_2)_2CH(Br)CH(CH_2CH_3)CH_3$?

<p>5-bromo-2,6-dimethyloctane (B)</p> Signup and view all the answers

What is the IUPAC name of the compound $(CH_3)_3C-C(CH_3)_2CH_2-CH(Cl)CH_3$?

<p>5-chloro-2,2,3,3-tetramethylhexane (A)</p> Signup and view all the answers

What is the IUPAC name for the compound $CH_3C(CH_3)_2(CH_2)_3C(CH_3)_3$?

<p>2,2,6,6-tetramethylheptane (B)</p> Signup and view all the answers

What are the two types of substituents in organic compounds?

<p>Inorganic and organic substituents (A)</p> Signup and view all the answers

In which order should substituents be listed when naming an alkane with multiple substituents?

<p>Inorganic groups first, followed by organic groups in alphabetical order (C)</p> Signup and view all the answers

How should the position of substituents on the parent chain be indicated?

<p>With the least possible numbers to minimize confusion (A)</p> Signup and view all the answers

What prefix is used to indicate two identical substituents?

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

How are numbers and names separated in chemical nomenclature?

<p>By commas for numbers and hyphens for names (B)</p> Signup and view all the answers

In the compound CH₃Cl, what is the IUPAC name?

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

Why might expanding a condensed structure be necessary?

<p>To determine the specific geometric arrangement (B)</p> Signup and view all the answers

Flashcards

Inorganic substituents

Substituents that contain atoms other than carbon and hydrogen, such as Cl, Br, I, NH2, NO2, OH, and CN.

Organic Substituents

Substituents that consist of alkyl groups, which are chains of carbon and hydrogen atoms. They have the general formula CnH2n-1.

Alphabetical order in naming

When naming a compound with multiple substituents, the substituents are listed in alphabetical order.

Least Possible Number

The position of each substituent in the parent chain is indicated by the lowest possible number.

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Multiple Substituents

If a substituent is present multiple times, Greek prefixes (di, tri, tetra, etc.) are used to indicate the number of occurrences.

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What is hybridization?

The process of mixing atomic orbitals to form new hybrid orbitals. These hybrid orbitals have equal energies and directional properties, and they optimize the overlap of orbitals, leading to stronger and more stable bonds.

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What is a sigma (σ) bond?

A single covalent bond formed by the direct overlap of two atomic orbitals, one from each participating atom. It is symmetrical and has the highest electron density along the axis connecting the two nuclei.

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Why does carbon form four C-Cl bonds in CCl4?

In CCl4, carbon forms four identical C-Cl bonds due to sp3 hybridization, where one 2s and three 2p orbitals combine to create four equivalent sp3 hybrid orbitals. Each sp3 orbital overlaps with a chlorine 3p atomic orbital, forming a strong sigma bond. These sp3 orbitals are oriented tetrahedrally, explaining the tetrahedral geometry of CCl4.

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How can carbon form 4 bonds when it only has 2 unpaired electrons?

Carbon has two unpaired electrons in its ground state, but it can form four bonds due to the promotion of one 2s electron to a 2p orbital. This creates four unpaired electrons, allowing carbon to form four covalent bonds.

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How are C-C sigma bonds formed in alkanes?

sp3-sp3 C-C sigma bonds are formed by the overlap of two sp3 hybrid orbitals, one from each carbon atom. The bond formed is a symmetrical and strong sigma bond.

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What are substituents in organic chemistry?

Substituents are atoms or groups of atoms attached to the main carbon chain of an organic molecule.

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What are inorganic substituents?

Inorganic substituents are groups that do not contain carbon. They are typically named using prefixes like chloro, bromo, and nitro.

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What are organic substituents?

Organic substituents are groups that contain carbon. They are primarily alkyl groups, such as methyl (CH₃) and ethyl (CH₂CH₃).

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What is the parent structure in organic nomenclature?

The parent structure is the longest continuous chain of carbon atoms in a molecule. The name of the parent structure determines the base name of the compound.

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How are substituent positions indicated?

The position of a substituent is indicated by a number, which tells you where on the parent chain it is located.

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How are substituents ordered in IUPAC names?

Substituents are listed in alphabetical order, regardless of whether they are inorganic or organic.

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How are multiple occurrences of the same substituent indicated?

Greek prefixes (di, tri, tetra, etc.) are used to indicate the number of times a particular substituent appears in the molecule.

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How is the IUPAC name of an organic molecule formed?

The IUPAC name of a molecule is formed by combining the parent structure name with the names and locations of all substituents.

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IUPAC Naming

The process of naming organic compounds using a systematic set of rules.

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Parent Chain

The longest continuous carbon chain in a molecule, determining the base name of the compound.

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Substituents

Branches or substituents attached to the parent chain, named and numbered according to their position.

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Locant

The position of a substituent on the parent chain, indicated by a number.

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Alkane

A type of organic compound containing a single bond between carbon atoms, forming a straight or branched chain.

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Volatility

The tendency of a substance to vaporize, or change from a liquid to a gas.

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Boiling point trend in alkanes

As the length of the carbon chain in an alkane increases, the boiling point also increases. This is because stronger van der Waals forces exist between the larger molecules.

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Branching and boiling point

Branching in alkane molecules decreases the boiling point. This is because branching reduces the surface area for intermolecular interactions, leading to weaker van der Waals forces.

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Intermolecular forces and volatility

The strength of the intermolecular forces (van der Waals forces) between alkane molecules determines their volatility. Stronger forces mean lower volatility.

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Branching and volatility

Volatility increases with increased branching in alkane molecules. This is because branching reduces the strength of van der Waals forces, making it easier for molecules to escape into the gas phase.

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Why are alkanes insoluble in water?

Alkanes are not soluble in water due to their non-polar nature and the strong hydrogen bonding in water molecules. The weak interactions between alkanes and water are not enough to overcome the energy required to break the hydrogen bonds in water.

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Why are alkanes soluble in non-polar solvents?

Alkanes are soluble in non-polar solvents like benzene and ether because they both have similar van der Waals forces, allowing for stronger intermolecular interactions.

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What determines the physical state of an alkane?

The physical state of an alkane is determined by its chain length. Short-chain alkanes (C1-C4) are gases, medium-chain alkanes (C5-C18) are liquids, and long-chain alkanes (C19 and above) are solids at room temperature.

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How does chain length affect boiling point of alkanes?

The boiling point of an alkane increases as the chain length increases. This is due to the stronger van der Waals forces that exist between longer chains.

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What is the color of alkanes?

All alkanes are colorless in their pure state because they do not absorb visible light.

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Addition Reaction

Reactions where two or more molecules combine to form a single product, typically involving the addition of a molecule across an unsaturated bond.

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Elimination Reaction

Reactions where atoms are removed from a molecule, often creating a double or triple bond in the product.

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Substitution Reaction

A chemical reaction where one atom or group is replaced by another atom or group in a molecule.

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Hydrogenation

A chemical reaction that involves the addition of a hydrogen molecule to a molecule, typically an unsaturated molecule, to form a saturated molecule.

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Dehydration

A chemical reaction that involves the removal of water from a molecule, often resulting in the formation of a double or triple bond in the molecule.

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What is a substitution reaction?

A chemical reaction in which an atom or group of atoms is replaced by another atom or group of atoms. Examples include halogenation reactions where a halogen atom replaces a hydrogen atom, and hydrolysis where a hydroxyl group replaces a halogen atom.

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Why are alkanes unreactive?

Alkanes are generally unreactive due to the strong covalent bonds between carbon and hydrogen atoms (C-H & C-C bonds). These bonds are nonpolar, meaning there's no readily available electron for reactions.

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Which compound will distill off first: heptane or hexane?

In distillation, hexane will vaporize first because it has a lower boiling point. This is due to its smaller size resulting in weaker van der Waals forces compared to heptane.

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What type of reactions do alkanes undergo?

Alkanes undergo substitution reactions where one atom or group of atoms is replaced by another. This is possible due to the high energy required to break the strong C-H and C-C bonds, leading to the substitution of a hydrogen atom with another atom or group.

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What are the other main reactions in organic chemistry?

The main reaction in organic chemistry are: Addition, elimination, and rearrangement. These reactions involve altering the structure of organic molecules by adding or removing atoms or groups.

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Homolytic cleavage

One electron from the bonding pair is transferred to each atom, forming highly reactive free radicals.

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Heterolytic cleavage

All bonding electrons are transferred to one atom, usually the more electronegative one, creating ions.

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Heterolytic fission

The breaking of a covalent bond where the electron pair moves completely to one atom, forming a carbocation and an anion. 

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Homolytic fission

The breaking of a covalent bond where each atom receives one electron, forming two free radicals.

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Covalent bond cleavage

The process where a covalent bond is broken, resulting in the formation of either ions or free radicals.

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Chain Reaction

A reaction that proceeds through a series of steps involving reactive intermediates, particularly free radicals. It is characterized by a chain initiation, propagation, and termination process. These reactions typically produce a variety of products, and their speed can be influenced by factors like light, temperature, and the presence of inhibitors.

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Chain Initiation

The first step in a chain reaction where free radicals are formed from stable molecules. This usually requires external energy, such as sunlight, to break bonds and generate reactive species.

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Chlorine Free Radical

A chlorine atom with an unpaired electron, making it highly reactive. These are formed during the initiation step and are responsible for propagating the chain reaction.

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Chain Propagation

A step in a chain reaction where free radicals react with molecules, creating new free radicals that continue the reaction. This process involves the transfer of atoms or groups between molecules.

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Chain Termination

The final steps in a chain reaction where free radicals combine to form stable molecules, ending the chain reaction. This can occur through various combinations of radicals.

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