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Organic Chemistry Readiness Quiz

Assess Your Fundamental Organic Chemistry Skills

Difficulty: Moderate
Questions: 20
Learning OutcomesStudy Material
Colorful paper art depicting elements of an Organic Chemistry Readiness Quiz.

Curious to gauge your organic chemistry fundamentals? This Organic Chemistry Readiness Quiz features 15 focused multiple-choice questions on functional groups, nomenclature, and reaction mechanisms. Perfect for students aiming to strengthen core concepts before advanced courses or standardized exams. You can easily tweak questions and layout in the editor to match your teaching style. Discover related challenges like the Chemistry Fundamentals Quiz, the Basic Chemistry Knowledge Quiz, or explore all quizzes.

Easy
Which functional group is present in CH3CH2OH?
Carboxylic acid
Alcohol
Ether
Aldehyde
Ethanol contains an - OH group characteristic of alcohols. This functional group is defined by a hydroxyl group bonded to a saturated carbon.
What is the product of hydrogenation of ethene (CH2=CH2) using H2/Pt?
Ethanol
Ethane
Ethene
Ethyne
Hydrogenation adds hydrogen across the double bond, converting the alkene to an alkane. Ethene is converted to ethane under these conditions.
Which of the following compounds is most acidic?
Acetic acid
Ethanol
Water
Phenol
Acetic acid has a pKa around 4.8, making it much more acidic than phenol or ethanol. The carboxylate anion is stabilized by resonance, enhancing acidity.
What is the IUPAC name for CH3-CH2-CH3?
Propene
Propane
Propanol
Butane
A three-carbon linear alkane is named propane. The suffix "-ane" indicates single bonds, and three carbons correspond to "prop-".
How many stereoisomers are possible for 2-butanol?
1
2
4
3
2-Butanol has one stereocenter at the second carbon. A single stereocenter yields two enantiomeric stereoisomers.
Medium
Which functional group is present in CH3CONH2?
Amine
Carboxylic acid
Ester
Amide
The CONH2 group defines an amide functional group. Amides feature a carbonyl bonded to a nitrogen.
In an SN2 reaction, which species acts as the nucleophile?
Cl−
H+
OH−
R+
SN2 mechanisms involve the nucleophile donating an electron pair to the electrophilic carbon. The hydroxide ion (OH−) is a strong nucleophile capable of attacking the substrate directly.
A tertiary alkyl halide reacts with a nucleophile under what mechanism?
E1
SN2
SN1
E2
Tertiary alkyl halides undergo SN1 reactions due to carbocation stability. Steric hindrance prevents backside attack, favoring the two-step SN1 mechanism.
What is the IUPAC name of (CH3)2CHCH3?
Butane
2-Methylpropane
2-Propanol
Isobutene
The main chain contains three carbons with a methyl substituent on the second carbon. This structure is correctly named 2-methylpropane.
How many geometric isomers does 2-butene have?
4
2
1
3
2-Butene can exist as cis and trans forms. Each isomer has distinct spatial arrangements around the double bond.
Which effect most stabilizes the acetate ion?
Hyperconjugation
Hydrogen bonding
Inductive donation from methyl
Resonance delocalization of negative charge over two oxygens
Delocalization of the negative charge over both oxygen atoms via resonance stabilizes the acetate ion. Resonance distributes electron density and lowers overall energy.
In the reaction of propene with HBr, which species acts as the electrophile?
Propene
H+
HBr
Br−
HBr ionizes into H+ and Br−. The alkene pi bond donates electrons to H+, so H+ is the electrophile.
In acid-catalyzed hydration of propene, which product is formed following Markovnikov's rule?
2-Propanol
Propanone
Propane
1-Propanol
Markovnikov's rule places the OH at the more substituted carbon. Hydration of propene yields 2-propanol.
A racemic mixture contains:
A meso compound
Equal amounts of enantiomers
Only diastereomers
Only one enantiomer
A racemic mixture contains both enantiomers in a 1:1 ratio. This mixture is optically inactive due to cancellation of rotation.
Which substituent exhibits the strongest inductive electron-withdrawing effect?
CH3
OCH3
CF3
NH2
CF3 has three highly electronegative fluorine atoms that pull electron density through the sigma bond. Other groups are less electron-withdrawing.
Hard
What is the IUPAC name for CH3-CH(CH3)-CH=CH-CH2-Cl?
5-Chloro-3-methylpent-2-ene
5-Chloro-2-methylpent-3-ene
4-Chloro-2-methylpent-1-ene
2-Chloro-4-methylpent-2-ene
The longest chain has five carbons (pent). The double bond is between C3 - C4, methyl at C2, and chloro at C5, giving 5-chloro-2-methylpent-3-ene.
In the nitration of nitrobenzene, the incoming electrophile attaches at which position relative to the existing NO2 group?
Meta
No substitution
Para
Ortho
The nitro group is strongly electron-withdrawing and deactivating. It directs electrophiles to the meta position by destabilizing ortho and para intermediates.
Which 2-butene isomer is more thermodynamically stable?
1-butene
trans-2-butene
Butane
cis-2-butene
Trans-2-butene is more stable due to reduced steric hindrance between the methyl groups compared to the cis isomer.
Which carbanion is most stabilized by resonance?
tert-Butyl carbanion
Allyl carbanion
Methyl carbanion
Vinyl carbanion
The allyl carbanion delocalizes the negative charge over three carbon atoms via resonance, greatly stabilizing it compared to localized carbanions.
How many stereoisomers are possible for 2,3-dichlorobutane?
3
2
1
4
2,3-Dichlorobutane has a meso form and an enantiomeric pair, giving a total of three distinct stereoisomers.
0
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Learning Outcomes

  1. Identify key functional groups in organic molecules.
  2. Predict outcomes of basic reaction mechanisms.
  3. Evaluate acid-base and electrophile-nucleophile interactions.
  4. Apply IUPAC nomenclature for simple compounds.
  5. Demonstrate understanding of stereochemistry and isomerism.
  6. Analyze resonance and inductive effects on stability.

Cheat Sheet

  1. Spotting Functional Groups - Become an organic chem detective by identifying alcohols, aldehydes, ketones, carboxylic acids, and amines at a glance. This foundation helps you predict molecular reactions and properties before diving into complex problems. Introduction to Resonance
  2. Decoding Reaction Mechanisms - Dive into nucleophilic substitutions (SN1 and SN2) and eliminations (E1 and E2) to see how reagents, solvents, and conditions sway each step. Learning the order of events unlocks clever shortcuts for exam problems. You'll feel like a reaction wizard by the end! Conjugation and Resonance in Organic Chemistry
  3. Acid-Base Interactions - Acidic and basic vibes come from how electron-withdrawing or donating groups shift electron density. Understanding this dance is key to predicting which protons will pop off and when molecules attack each other. This skill turns guesswork into crystal-clear reasoning. Electron-withdrawing group
  4. IUPAC Nomenclature - Naming molecules with confidence means mastering IUPAC rules and spotting the longest chains, functional priorities, and correct suffixes. Practice with simple structures, then level up to branched or multifunctional compounds. Soon, trivial names won't stand a chance against your systematic naming skills! Inductive effect
  5. Stereochemistry Basics - Stereochemistry is where molecules show off their 3D personalities - chirality, enantiomers, and diastereomers rule this world. Grasping these differences helps you predict interactions in everything from drug design to material science. It's like understanding the secret handshake of molecules. Mesomeric effect
  6. Resonance Analysis - Drawing all possible resonance forms reveals the real electron distribution in a molecule. By comparing contributors, you'll know which structure has the most sway over stability. This analysis sharpens your intuition for reactivity trends. Introduction to Resonance
  7. Inductive Effect Mastery - The inductive effect describes how sigma bonds ferry electron pull or push through a molecule's backbone. Recognizing this tug-of-war helps explain why certain sites are reactive hotspots. It's the secret behind many reaction mechanisms. Inductive effect
  8. Mechanism Drawing Practice - Get comfy with curved arrows showing electron movement in reaction mechanisms. Each arrow tells a story of bond-breaking and bond-making - like a visual screenplay for organic transformations. By practicing, you build an intuitive map of how reactions really happen. Introduction to Resonance
  9. Hybridization Hustle - Hybridization (sp, sp2, sp3) shapes molecular geometry, bond angles, and even acidity. Knowing these orbital mixes helps you predict whether a molecule is linear, trigonal, or tetrahedral. It's the key to visualizing structures in 3D. Conjugation and Resonance in Organic Chemistry
  10. Mesomeric Magic - The mesomeric effect shines a light on how electrons delocalize through π-systems and lone pairs. This resonance-driven phenomenon can stabilize or activate parts of a molecule in surprising ways. Mastering it will elevate your understanding of aromatic compounds and beyond. Mesomeric effect
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