Questions and Answers
What is the expected major product from the following reaction: Br2, H2O?
What is the expected major product for the following reaction sequence?
What is the expected major product of the reaction sequence shown below?
What was the starting material used to produce the dial shown under the conditions given?
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Which reagent would you use to accomplish the transformation shown here?
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What is the expected major product resulting from treatment of (E)-3-methyl-3-hexene with Br2 in the presence of methanol?
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Identify the expected major organic product resulting from the following reaction sequence.
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Which reagent would you use to accomplish the following transformation?
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Which of the following is a propagation step in the free-radical bromination of methane?
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What is the major product of the following reaction?
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Predict the major product of the following reaction?
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Given the relative reactivities of various kinds of hydrogens, the major product expected from mono-chlorination of 2-methylbutane would be what?
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How many different products will result if radical monobromination of the following compound only occurs at 3o carbons?
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Predict the major product from addition of two equivalents of HBr in the following reaction.
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Free radical chlorination of ethane can produce higher halogenation products such as dichloroethane, trichloroethane, tetrachloroethane, pentachloroethane, and hexachloroethane. How could the production of higher halogenated products be minimized?
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Which of the following is the rate determining step in the free-radical bromination of methane?
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How many constitutional isomers can be formed from the monochlorination of the hydrocarbon shown below?
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What major product would result from the following sequence of reactions?
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What would be the expected major product of the following reaction?
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Which is the major product of combining 1,3-butadiene with HBr at 25C?
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Select all the molecules that should be aromatic
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Azulenes are soluble in strong aqueous acids because of a reactions with H+. Which of the structures below would represent the most stable form of protonated azulene?
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What will be the major product of the following reaction?
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How many different dichlorophenols are possible?
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Is the following molecule aromatic, anti-aromatic, or nonaromatic?
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Predict the product for the following reaction.
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Which of the following reactions of aromatics is reversible?
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What major product would you expect from the following reaction?
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What is the major product of the following reaction?
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Predict the major product of the following reaction: Br2, FeBr3
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What would be the major product from the following reaction sequence?
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What major product(s) would you expect from the reaction shown?
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Carefully consider the effect of the nitro groups on the stability of the intermediates involved as you decide which product(s) the reaction shown provides.
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Predict the product for the following reaction sequence.
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Predict the major organic product of the following reaction sequence.
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Predict the product of the following reaction.
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What would the major product of the following reaction?
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Which proton in the following molecule is the most acidic?
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Predict the major organic product of the following reaction sequence.
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Predict the product of the following reaction.
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What product is formed in the aldol condensation of propanal?
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What would you expect the result from the following reaction?
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Which product would you not expect the crossed aldol reaction between acetaldehyde and propionaldehyde?
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The best reactants to convert cyclohexanone to 2-methylcyclohexanone cleanly would be:
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Which of the following sets of reaction conditions will result in the following transformation?
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Predict the major organic product of the following reaction.
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What major product would you expect when the following diketone undergoes aldol cyclization in base, followed by acid?
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Study Notes
General Concepts in Organic Chemistry Reactions
- Hydrohalogenation reactions involve the addition of HX (where X is a halogen) to alkenes, leading to the formation of carbocation intermediates.
- The stability of carbocations is influenced by their degree (primary, secondary, tertiary) and the presence of electron-donating groups which can stabilize the positive charge.
Reaction Products
- Major products from reactions can be predicted based on regioselectivity and stereoselectivity of reactions such as hydrohalogenation and addition of halogens.
- The addition of Br2 and H2O typically leads to the formation of bromohydrin products.
- Radical reactions like chlorination can produce multiple halogenated products, and understanding the reactivity of hydrogens (primary, secondary, tertiary) is crucial for predicting major products.
Stability and Reactivity of Intermediates
- Stabilization of radicals and carbocations impacts the product distribution in reactions. For example, tertiary radicals are more stable than secondary, which are more stable than primary.
- Carbanions and radicals can be ranked based on stability to predict reaction pathways in nucleophilic substitutions (SN1, SN2).
Aromaticity and Electrophilic Substitution
- Aromatic compounds exhibit unique stability due to resonance; only cyclic, planar structures with complete conjugation are aromatic.
- Electrophilic aromatic substitution reactions involve the substitution of a hydrogen atom on an aromatic ring, often following a two-step mechanism where a sigma complex (arenium ion) is formed.
Diels-Alder Reactions
- The Diels-Alder reaction is a cycloaddition between a diene and a dienophile, leading to the formation of six-membered rings. Reactivity depends on the substituents on both diene and dienophile.
Organic Functional Group Transformations
- Different reagents are used for specific transformations, including additions, oxidations, and reductions; familiarization with these reagents and the context of their use is essential.
- Common reactions in organic chemistry can include aldol condensation and cyclization reactions that yield specific products based on the structure of the starting materials.
Acid-Base Reactions
- Acidity can be compared by assessing the stability of the conjugate base formed after deprotonation.
- The presence of electronegative substituents can increase acidity due to their ability to stabilize negative charges.
Synthesis and Mechanism Predictions
- Predicting the major products of reactions often requires knowledge of reaction mechanisms, including regioselectivity and stereochemistry.
- Systematic naming and the application of IUPAC rules are critical for accurately describing organic compounds and their transformations.
Isomerism in Organic Compounds
- Constitutional isomerism refers to different compounds with the same molecular formula but different connectivity, which can be explored through reactions such as free-radical halogenation.
Key Terms
- Enantiomers: Molecules that are non-superimposable mirror images of each other.
- Thermodynamic vs Kinetic Products: Thermodynamic products are more stable and formed at equilibrium; kinetic products are formed faster but might be less stable.
- Propagation Steps: Steps in radical reactions that sustain the radical chain reaction process.
Summary
- Understanding the stability of intermediates, reactivity of various carbocation and radical types, and the mechanisms of reactions like electrophilic aromatic substitution and Diels-Alder will improve predictions of reaction outcomes in organic chemistry.
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Description
Test your knowledge on organic chemistry concepts with these flashcards. Focus on carbocations, reaction products, and mechanisms. Ideal for revising key reactions and understanding stability in organic compounds.
