Organic Chemistry: Alkanes and Functional Groups

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Questions and Answers

What is the name of the alkane with 7 carbon atoms?

  • Nonane
  • Octane
  • Hexane
  • Heptane (correct)

The suffix of an alkane name indicates the functional group present in the molecule.

False (B)

What is the name of the branched substituent with the formula CH3CH2CH?

sec-butyl

The longest carbon chain in a molecule is called the ______ chain.

<p>parent</p> Signup and view all the answers

Match the following substituents with their corresponding structures.

<p>isopropyl = CH3CHCH3 CH3 sec-butyl = CH3CH2CH2CH3 tert-butyl = CH3 CH3C CH3 isobutyl = CH3 CH3CHCH2</p> Signup and view all the answers

The IUPAC name of an acid amide is formed by replacing the '-e' in the name of the _______ alkane with '-amide'.

<p>parent</p> Signup and view all the answers

The IUPAC name of an alkyl nitrile is formed by adding the suffix '-nitrile' to the name of the parent alkane.

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

What is the IUPAC name of the acid chloride derived from propanoic acid?

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

What is the functional group present in acid chlorides?

<p>COCl</p> Signup and view all the answers

Match the following compounds with their corresponding functional group:

<p>HCONH2 = Amide CH3CH2CONH2 = Amide CH3C≡N = Nitrile CH3CH2COCl = Acid Chloride</p> Signup and view all the answers

What is the common name of the acid amide derived from butanoic acid?

<p>Butyramide</p> Signup and view all the answers

Which of the following is NOT a common name for an alkyl nitrile?

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

The functional group -C≡N is associated with ______.

<p>nitriles</p> Signup and view all the answers

Which of the following is the IUPAC name for CH3CH2OHCH2OH?

<p>Propane 1, 2-diol (D)</p> Signup and view all the answers

The general formula for ethers is CnH2n+1-O-CmH2m+1, where n and m can represent the same or different numbers.

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

What is the common name for the ether with the molecular formula CH3OCH3?

<p>Dimethyl ether</p> Signup and view all the answers

Which of the following solvents would result in the highest enol content for acetoacetic ester?

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

In the IUPAC system for naming aldehydes, the suffix '-al' is added to the parent ______ name.

<p>alkane</p> Signup and view all the answers

The enol content of pentană2,4ădione (CH3COCH2COCH3) is found to be ______% and ______% at 27.5Ĉ and 275.5ĈC respectively.

<p>95, 45</p> Signup and view all the answers

The anion formed when a strong base is added to a ketone with an -hydrogen atom is the same regardless of whether the ketone or enol form reacts.

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

Match the following functional groups with their corresponding IUPAC suffix:

<p>Alcohol = -ol Ether = -ether Aldehyde = -al</p> Signup and view all the answers

Which of the following statements is true about alkoxy-alkanes?

<p>They are formed by replacing a hydrogen atom in an alkane with an alkoxy group. (B)</p> Signup and view all the answers

Explain why the enol content of acetoacetic ester is lower in water than in toluene.

<p>Water reduces the enol content of acetoacetic ester by hydrogen bonding with the carbonyl group, making it less available for intramolecular hydrogen bonding, which stabilizes the enol form. This decreases the proportion of the enol form in water compared to toluene.</p> Signup and view all the answers

Match the following solvents with their corresponding enol content for acetoacetic ester:

<p>Water = 15% Toluene = 19.8% Hexane = 92% MeCN = 58%</p> Signup and view all the answers

The IUPAC name for CH3CH2OCH3 is Methoxymethane.

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

What is the functional group present in aldehydes?

<p>CHO</p> Signup and view all the answers

Which of the following is NOT a factor that contributes to the stability of an enol form compared to a keto form?

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

In the keto form of a molecule, the Ar-C-Ar bond angle is typically wider than in the enol form.

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

What is the name of the phenomenon responsible for the increased stability of the enol form due to the interaction of the double bond with a carbonyl group?

<p>Cross-conjugation</p> Signup and view all the answers

The enol form of 2,2-dimesitylenthanal is favored over the keto form due to the ______ of the bulky aryl groups.

<p>steric repulsion</p> Signup and view all the answers

Match the following terms with their definitions:

<p>Cross-conjugation = Interaction between a double bond and a carbonyl group, enhancing enol stability Intramolecular hydrogen bonding = Hydrogen bonding within the same molecule, contributing to enol stability Aromatic stabilization = Stabilization of a molecule due to the presence of a delocalized pi system, favoring enol forms Steric repulsion = Repulsion between bulky groups, leading to a preference for the enol form in certain cases</p> Signup and view all the answers

What type of hydrogen bonding can occur in an enol form, contributing to its stability?

<p>Intramolecular hydrogen bonding</p> Signup and view all the answers

The enol form in general is always less stable than the keto form.

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

Which of the following factors can influence the equilibrium between the keto and enol forms?

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What is the characteristic functional group for alkynes?

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

The prefix 'bis' is used to indicate the presence of two identical substituents on a molecule.

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

What is the IUPAC name of the compound with the structure CH3CH2CH2CH(CH3)CH2CH3?

<p>3-methylhexane</p> Signup and view all the answers

The functional group in the compound CH3CH2CH2CHO is an ______ group.

<p>aldehyde</p> Signup and view all the answers

Match the following functional groups with their corresponding symbols:

<p>Aldehyde = =O Ketone = -OH Carboxylic acid = -CHO Alcohol = ≡ Alkynes = -COOH</p> Signup and view all the answers

What is the IUPAC name of the compound with the structure CH3CH2CH2CH2CH2CH2CH(CH3)CH2CH2CH2CH3?

<p>8-methyldodecane (A)</p> Signup and view all the answers

The suffix 'ol' is used to indicate the presence of an alkene group in a molecule.

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

What is the IUPAC name of the compound with the structure CH3CH2CH2COCH2CH3?

<p>3-hexanone</p> Signup and view all the answers

Which of the following factors contributes to the increased stability of the enol form of 2,2-dimesitylenthanal compared to its keto form?

<p>The bulky aryl groups experience less steric repulsion in the enol form. (B), The enol form is stabilized by intramolecular hydrogen bonding. (C), The enol form exhibits aromatic stabilization. (D)</p> Signup and view all the answers

In general, the enol form of a molecule is always more stable than the keto form.

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

In the keto form of 2,2-dimesitylenthanal, the Ar-C-Ar bond angle is approximately ______ degrees, while in the enol form, it is ______ degrees.

<p>109, 120</p> Signup and view all the answers

Flashcards

Alkane Naming

Alkane names reflect the carbon count and functional groups.

Parent Chain

The longest continuous carbon chain in an alkane.

Substituents

Atoms or groups attached to the parent chain of an alkane.

Saturated Hydrocarbons

Hydrocarbons with single bonds only, full as possible.

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Common Branched Substituents

Familiar groups like isopropyl and butyl which branch off alkanes.

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Enolization

The conversion of a carbonyl compound to its enol form.

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Effect of Solvent on Enol Content

Different solvents can stabilize either the enol or keto form, affecting their relative proportions.

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Hydrogen Bonding in Enols

Intramolecular hydrogen bonding stabilizes enols but is less effective in polar solvents like water.

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Keto vs. Enol Stability

Keto forms are usually more stable due to solvation effects, especially in polar environments.

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Canonical Forms

The anion resulting from enolization and keto forms is the same; they differ only in electron placement.

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Alkynes

Hydrocarbons with a triple bond between carbon atoms, indicated by 'yne'.

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Functional Group Prefixes

First prefix indicates carbon not in longest chain; second indicates it is.

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Bis-

Indicates the presence of two identical functional groups in a compound.

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Cycloalkane Naming

Cycloalkanes are numbered from the side of the cyclic group in the name.

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di-

Prefix used to indicate two identical substituents in a molecule.

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Carboxylic Acid

Organic compounds containing a carboxyl group (-COOH).

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Aromatic Compounds

Compounds that contain one or more aromatic rings with special stability.

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Dione

A compound containing two carbonyl groups (C=O).

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IUPAC name of acid amide

Derived from the parent alkane by replacing 'e' with 'amide'.

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Common name of methanamide

Also known as formamide, derived from formic acid.

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Structure of alkane nitriles

General formula is R-C≡N with a functional group C≡N.

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Naming of alkyl cyanide

IUPAC name adds '-nitrile' to the parent alkane's name.

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Definition of acid chlorides

Compounds with the functional group RCOCl; derived from carboxylic acids.

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General formula for acid chlorides

CnH2n+1COCl, where n is 0, 1, 2...

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Suffix for acid chlorides

The suffix '-oyl chloride' is used in IUPAC naming.

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IUPAC name for ethanamide

Commonly known as acetamide, derived from acetic acid.

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Polyhalo compound

A compound with multiple halogen atoms attached to a parent alkane.

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Ether

An alkoxy derivative of alkanes with the general formula R-O-R'.

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Alkoxy group

An alkyl group connected to an oxygen atom.

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Simple ether

An ether with identical alkyl groups (R = R').

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Mixed ether

An ether with different alkyl groups (R ≠ R').

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Alkoxyalkane

Produced when a hydrogen in an alkane is replaced by an alkoxy group.

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Aldehyde

A compound with the general formula CnH2n+1CHO.

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IUPAC nomenclature

Systematic method for naming organic compounds based on structure.

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Keto form

A form of a compound with a carbonyl group (C=O).

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Enol form

A form of a compound with a hydroxyl group (C=C-OH).

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Cross-conjugation

Interaction between non-adjacent pi systems in molecules.

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Intramolecular hydrogen bonding

A hydrogen bond occurring within the same molecule.

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Steric repulsion

The force that causes atoms to repel each other due to size.

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Aromatic stabilization

A stabilization resulting from the delocalization of electrons in cyclic structures.

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Aryl groups

Functional groups derived from aromatic rings.

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Bond angle adjustment

The change in angle between bonds when transitioning forms.

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Study Notes

General Organic Chemistry Content

  • This document covers various aspects of general organic chemistry, including nomenclature, classifications of organic compounds, homologous series, and isomerism. The document also discusses various functional groups and reactions.

Nomenclature of Organic Compounds

  • Nomenclature involves assigning names to organic compounds systematically.
  • IUPAC (International Union of Pure and Applied Chemistry) rules are used for systematic naming.
  • Names generally consist of a prefix, word root, primary suffix and secondary suffix.

Classification of Organic Compounds

  • Organic compounds are broadly classified as acyclic (open-chain) and cyclic (closed-chain) compounds.
  • Acyclic or aliphatic compounds have open chains, which could be either branched or unbranched..
  • Cyclic or carbocyclic compounds have closed chains of carbon atoms, with alicyclic compounds resembling acyclic compounds in properties, and aromatic compounds having alternate single and double bonds. (e.g. benzene)
  • Heterocyclic compounds have atoms other than just carbon in the ring.

Homologous Series

  • Homologous series are a series of organic compounds with a gradual gradation in physical and chemical properties.
  • Successive members differ by CH₂ and by a mass of 14 units.
  • Example: Alkanes, Alkenes, Alkynes, Alcohols, Aldehydes, Ketones, and Carboxylic acids.
  • Each homologous series commonly shares a formula.

Isomerism

  • Isomers are compounds with the same molecular formula but different structures.
  • Structural isomerism involves differences in the arrangement of atoms within the molecule.
  • Chain/Nuclear isomers have different carbon atom arrangements.
  • Positional isomers have the same carbon arrangement, but a functional group at a different position.
  • Functional isomers have the same atoms, but different functional groups.
  • Stereoisomers have the same structural formula but different spatial arrangements of atoms or groups in space.
  • Geometrical isomerism is caused by the restricted rotation around a double bond.
  • Optical isomerism refers to non-superimposable mirror images.
  • Conformational isomers result from rotation around a single bond.

Other Topics

  • The document also covers topics like:
  • Haloalkanes
  • Alkanols
  • Alkanediols
  • Alkoxyalkanes (Ethers)
  • Alkanals (Aldehydes)
  • Alkanones (Ketones)
  • Alkanoic Acids
  • Alkanedioic Acids
  • Alkanamides
  • Alkyl Cyanides
  • Alkyl nitriles
  • Alkanoyl chlorides (Acid Chlorides)
  • Alkylakanoates (Esters)
  • Nitroalkanes

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