Organic Chemistry: Nomenclature Quiz

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Questions and Answers

What suffix is used for carbon substituents?

-yl (correct)

-ene

-ic

-ane

When naming substituents, numerical prefixes are considered when determining alphabetical order.

False

What should be used before each substituent to indicate its location on the parent chain?

Chain number and a hyphen

For multiple identical substituents, the prefix used is __________.

di- tri- tetra- Signup and view all the answers

Match the prefix with its meaning in organic nomenclature:

di- = Two tri- = Three tetra- = Four penta- = Five Signup and view all the answers

Which of the following steps is NOT correct when naming complex substituents?

Number the carbons starting from the end farthest from the parent chain. Signup and view all the answers

The name of the parent chain should be separated with a space from the substituents.

False Signup and view all the answers

What is the primary consideration when identifying the longest carbon chain in a complex substituent?

Most substituents Signup and view all the answers

What should be used to indicate multiple identical substituents in a compound name?

Use of the numerical prefix di-, tri-, tetra-, etc. Signup and view all the answers

The name of a complex substituent should not be enclosed in parentheses.

False Signup and view all the answers

What prefix should be used to name a bicyclic compound?

bicyclo- Signup and view all the answers

The parent chain name for a bicyclic compound ends with the name of the corresponding alkane that includes all carbon atoms in the ______.

ring system Signup and view all the answers

Which of the following names is the correct systematic name for isobutyl?

1-methylpropyl Signup and view all the answers

When naming substituents, the list should be in numerical order of the substituent count.

False Signup and view all the answers

To name a bicyclic compound, the number of carbon atoms between bridgeheads is listed in ______ from highest to lowest.

brackets Signup and view all the answers

Match the complex substituent with its systematic name:

isopropyl = 1-methylethyl sec-butyl = 2-methylpropyl tert-butyl = 1,1-dimethylethyl isobutyl = 1-methylpropyl Signup and view all the answers

What prefix is used to indicate a spiro compound in naming?

spiro- Signup and view all the answers

The suffix for a carboxylic acid is -ol.

False Signup and view all the answers

What do you call the compounds that have non-superimposable mirror images?

Chiral compounds Signup and view all the answers

In naming spiro compounds, the two numbers representing carbon atoms in each ring are listed in ________ order.

lower to higher Signup and view all the answers

Match the functional group with its correct suffix:

Alcohol = -ol Amine = -amine Aldehyde = -al Ester = -oate Signup and view all the answers

Which suffix is used for an ester in nomenclature?

-oate Signup and view all the answers

Substituents are listed before the parent chain when naming bicyclic compounds.

True Signup and view all the answers

Number the parent chain starting from the carbon adjacent to the spiro-carbon as #1, continuing through the ________ ring.

smaller Signup and view all the answers

What is the prefix used for a nitrile functional group?

cyano- Signup and view all the answers

What type of compound is characterized by having a -thiol functional group?

Thiol Signup and view all the answers

Which of the following correctly describes the naming of substituents in an organic compound?

Substituents should be listed in alphabetical order using the first letter of the complex substituent’s name. Signup and view all the answers

The name of the parent chain for a bicyclic compound does not include the number of carbon atoms between bridgeheads.

False Signup and view all the answers

What should be used as a locator before each substituent when naming an organic compound?

Chain number and a hyphen Signup and view all the answers

When naming multiple identical substituents, the prefix _______ is used.

di- Signup and view all the answers

Match the common complex substituents with their systematic names:

Isopropyl = 1-methylethyl Isobutyl = 2-methylpropyl Sec-butyl = 1-methylpropyl Tert-butyl = 1,1-dimethylethyl Signup and view all the answers

Which prefix is used to start the name of the parent chain in bicyclic compounds?

bicyclo- Signup and view all the answers

The name of a complex substituent should always be separated by a space from the longest chain name.

False Signup and view all the answers

In the naming of bridged bicyclic compounds, how should the number of carbon atoms between bridgeheads be listed?

In brackets from highest to lowest Signup and view all the answers

Which type of solvent is preferred for E1 reactions?

Polar aprotic solvents Signup and view all the answers

Rearrangements are possible in E1 reactions.

True Signup and view all the answers

What is the reactivity order for electrophiles in SN2 reactions?

CH3 > 1° > 2° Signup and view all the answers

Which acid is used to remove amines in acid/base extractions?

HCl Signup and view all the answers

Fractional distillation is equivalent to performing multiple simple distillations.

True Signup and view all the answers

In E2 reactions, a strong ______ is required.

base Signup and view all the answers

What type of chromatography involves separation primarily due to differences in boiling points?

Gas chromatography (GC) Signup and view all the answers

Match the reaction type with its characteristic:

SN1 = Weak nucleophile, polar protic solvent SN2 = Strong nucleophile, polar aprotic solvent E1 = Weak base, possible rearrangements E2 = Strong base, anti-periplanar elimination Signup and view all the answers

In Recrystallization, solute has a higher solubility at _______ temperatures.

high Signup and view all the answers

Which nucleophile would be considered weak?

H2O Signup and view all the answers

Match the spectroscopy technique with its function:

IR Spectroscopy = Identifies functional groups based on bond vibration Mass Spectrometry = Analyzes the mass and fragmentation of molecules NMR Spectroscopy = Provides information about the structure of organic compounds UV-Vis Spectroscopy = Analyzes the absorbance of UV or visible light Signup and view all the answers

In E2 reactions, stereochemistry has no impact on elimination.

False Signup and view all the answers

Which of the following is NOT a type of chromatography mentioned?

Liquid Chromatography Signup and view all the answers

What is the importance of leaving groups in substitution reactions?

Good leaving groups facilitate better reactivity for SN1 and SN2 reactions. Signup and view all the answers

Phenols can be removed by using sodium bicarbonate (NaHCO3) in an acid/base extraction.

False Signup and view all the answers

The selectivity in free radical halogenation is highest for ______.

bromination Signup and view all the answers

What is the peak range for the C=O bond in IR spectroscopy?

~1710 cm-1 Signup and view all the answers

Which of the following nucleophiles is categorized as a strong nucleophile?

RO- Signup and view all the answers

In gas chromatography, the compound with a lower boiling point is _______ first.

eluted Signup and view all the answers

Which statement about simple distillation is true?

It is suitable if there is one major component. Signup and view all the answers

Which reaction condition generates a syn addition of hydroxyl groups to an alkene?

<ol> <li>OsO4</li> </ol> Signup and view all the answers

The addition of HBr in the presence of peroxides leads to Markovnikov addition.

False Signup and view all the answers

What type of ion is formed during the bromination of an alkene using Br2/CCl4?

bromonium ion Signup and view all the answers

The intermediate formed when using Hg(OAc)2 followed by NaBH4 in alkene reactions is a _______ ion.

mercurinium Signup and view all the answers

Match the alkene reaction conditions with their regioselectivity:

HBr = Markovnikov BH3.THF = Anti-Markovnikov Br2/H2O = Markovnikov H2/catalyst = No regioselectivity Signup and view all the answers

What is the correct order of mechanisms in bromination?

Initiation, Propagation, Termination Signup and view all the answers

Diels-Alder reactions involve anti addition of the diene and dienophile.

False Signup and view all the answers

What is the criteria for a compound to be considered aromatic?

Cyclic, conjugated, no sp3-hybridized atoms, planar, 4N+2 π electrons Signup and view all the answers

Alcohols are recognized by the suffix ______ when used as the main functional group.

ol Signup and view all the answers

Match the reaction type with its correct description:

Nitration = Electrophilic aromatic substitution with nitronium ion Friedel-Crafts Acylation = Reacts with an acyl chloride or anhydride Williamson Ether Synthesis = Creates ethers via SN2 reaction Clemmenson Reduction = Reduces ketones to alkanes using zinc and hydrochloric acid Signup and view all the answers

Which of the following statements about phenols is true regarding their acidity?

The acidity of phenols is higher than that of simple alcohols Signup and view all the answers

The addition of Grignard reagents to acid chlorides results in ketones.

False Signup and view all the answers

What are the products of the acid-catalyzed aldol condensation?

β-hydroxy aldehydes or ketones Signup and view all the answers

Match the compounds with their corresponding functional groups:

Aldehyde = -al ending Ketone = -one ending Alcohol = -ol ending Amine = -amine ending Signup and view all the answers

Study Notes

IUPAC Nomenclature Rules

Substituents must be numbered for proper identification along the parent chain.
Rank substituents alphabetically when tied at chain locations, comparing the first substituent found in both numbering directions.
Common carbon substituents end with "-yl" (e.g., methyl, ethyl).
For identical substituents, use prefixes (di-, tri-, tetra-) and indicate chain locators with a hyphen.
The final compound name combines substituents and the parent chain with no spaces.

Naming Complex Substituents

Identify the longest carbon chain of the complex substituent starting with the carbon attached to the parent as #1.
Number carbons in the longest chain sequentially from #1.
List substituents alphabetically, using chain locators before each and applying the same rules for identical substituents.
The name concludes with "-yl" suffix representing the longest chain, enclosed in parentheses.

Common Complex Substituents

Isopropyl (1-methylethyl)
Isobutyl (2-methylpropyl)
Sec-butyl (1-methylpropyl)
Tert-butyl (t-butyl, 1,1-dimethylethyl)

Naming Bicyclic Compounds

List substituents before the parent chain.
Use "bicyclo-" prefix for the parent chain, followed by the count of carbons between bridgehead carbons.
End with the alkane name reflecting total carbons in the ring system.
Number starting from one bridgehead, prioritizing the longest path.

Naming Spiro Bicyclic Compounds

Precede the parent name with "spiro-" and list the number of carbons in each ring, excluding the spiro carbon.
Complete the name with the alkane name for all carbons, including the spiro carbon.
Number starting from the smaller ring adjacent to the spiro-carbon for lower chain locator.

Nomenclature of Common Functional Groups

Carboxylic Acid: "-oic acid" (e.g., ethanoic acid)
Ester: "-oate" (e.g., ethyl propanoate)
Amide: "-amide" (e.g., ethanamide)
Nitrile: "-nitrile" (e.g., propanenitrile)
Aldehyde: "-al" (e.g., propanal)
Ketone: "-one" (e.g., propan-2-one)
Alcohol: "-ol" (e.g., propan-2-ol)
Amine: "-amine" (e.g., propan-2-amine)

Stereochemistry Vocabulary

Chiral compounds have non-superimposable mirror images termed enantiomers, indicating optical activity.

Nomenclature Rules

For multiple identical substituents, use locators separated by commas and prefixes such as di-, tri-, or tetra-.
List substituents in alphabetical order using the first letter of the complex substituent's name.
Name ends with the longest chain using a -yl suffix, no space between substituents and chain name.
Complex substituents should be named using the appropriate locator and enclosed in parentheses for the parent chain.

Common Complex Substituents

Isopropyl (1-methylethyl)
Isobutyl (2-methylpropyl)
Sec-butyl (1-methylpropyl)
Tert-butyl (1,1-dimethylethyl)

Naming Bicyclic Compounds

Substituents named similarly to alkanes, starting with the bicyclo- prefix.
List the number of carbons between bridgehead carbons in each path, in brackets from highest to lowest.
Parent chain named with alkane name that includes all carbons in the ring system.

Acid/Base Extractions

Amines extracted with HCl.
Carboxylic acids removed using NaHCO3 or NaOH.
Phenols extracted with NaOH.

Distillation Techniques

Simple Distillation: Best for liquids with a large boiling point difference (>100ºC) and when one major component exists.
Fractional Distillation: Equivalent to conducting multiple simple distillations.

Chromatography Methods

Gas Chromatography (GC): Separation based on boiling points; lower boiling compounds elute first.
Thin Layer Chromatography (TLC): Separation via polarity; more polar compounds have lower Rf values.
Column Chromatography: Similar to TLC; polarity-based retention time.

Recrystallization

Utilizes differences in solubility; higher solubility at high temperatures results in purifications.

Infrared (IR) Spectroscopy

Detects vibrational transitions in chemical bonds to identify functional groups.
Common absorption peaks for various bonds:
- Aromatic C-C: 1500-1600 cm⁻¹
- C=O: ~1710 cm⁻¹ (can shift for esters)
- O-H (alcohol): ~3400 cm⁻¹ (broad peak)

Mass Spectrometry

Involves electron ejection leading to molecule fragmentation.

Reaction Mechanisms

E1: Occurs with a tertiary electrophile, requires a strong base, favors polar aprotic solvents.
E2: Reactions favor anti-periplanar arrangement, possible with strong bases.

Free Radical Halogenation

Utilizes Cl₂ or Br₂ for the selective addition of halogens to alkenes; mechanisms include initiation, propagation, and termination.

Diels-Alder Reaction

A 4+2 cycloaddition involving a diene and a dienophile, characterized by a concerted mechanism and syn addition.

Criteria for Aromatic Compounds

Must be cyclic, conjugated, planar, and contain 4N+2 π electrons.
Antiaromatic compounds have 4N π electrons and exhibit instability.

Electrophilic Aromatic Substitution (EAS)

Key reactions include nitration, sulfonation, and Friedel-Crafts reactions, with specific electrophiles for each.

Alcohols and Ethers

Alcohols are named with an -ol suffix, ethers as alkoxy or alkyl alkyl ethers.
Phenols have distinct acidity compared to other alcohols; acidity trend: methyl > 1º > 2º > 3º.

Carbonyl Compounds

Aldehydes end in -al, and ketones end in -one.
Carbonyls react with alcohols to form hemiacetals/acetal, 1º amines to form imines, and undergo nucleophilic addition reactions.

Carboxylic Acids and Derivatives

Nomenclature features the -oic acid suffix for primary functionalities.
Reactivity order in nucleophilic acyl substitution: acid chlorides > anhydrides > esters/carboxylic acids > amides.

Alpha Substitution Reactions

Involve enolates formed from carbonyl compounds through keto/enol tautomerism.
Aldol reactions occur via enolate or enol addition, and Claisen condensation involves enolate addition to esters.

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Description

Test your knowledge of organic chemistry nomenclature rules. This quiz focuses on the proper ranking of substituents in aliphatic hydrocarbons based on their location and alphabetical order. Challenge your understanding of pentane, hexane, heptane, and octane structures.