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On being heated with a solution of sodium ethoxide in ethanol, compound \(\mathrm{A}\left(\mathrm{C}_{7} \mathrm{H}_{15} \mathrm{Br}\right)\) yielded a mixture of two alkenes \(\mathrm{B}\) and \(\mathrm{C}\), each having the molecular formula \(\mathrm{C}_{7} \mathrm{H}_{14}\). Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.

Short Answer

Expert verified
A is 3-ethyl-2-bromopentane; B is 3-ethyl-1-hexene; C is 4-ethyl-2-pentene.

Step by step solution

01

Identify Reaction Type

When compound A reacts with sodium ethoxide in ethanol, it undergoes dehydrohalogenation to form alkenes B and C. This is an elimination reaction.
02

Determine the Structure of Alkenes

Since both B and C have the molecular formula \( \mathrm{C}_{7} \mathrm{H}_{14} \), they are isomeric alkenes formed by different possible eliminations from compound A.
03

Analyze Hydrogenation Product

Hydrogenation of both B and C yields 3-ethylpentane. This indicates that both B and C must have double bonds located such that they reduce to this specific alkane.
04

Structure Deduction for Alkenes

To get 3-ethylpentane by hydrogenation, possible structures for B and C are 3-ethyl-1-hexene and 4-ethyl-2-pentene, considering that a double bond in either compound would lead to 3-ethylpentane after saturation.
05

Determine Structure of Compound A

Compound A must be able to form both \( \mathrm{B} \) and \( \mathrm{C} \). A likely candidate is 3-ethyl-2-bromopentane. This compound aligns with the elimination to the alkenes B and C stated above.

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Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Dehydrohalogenation
Dehydrohalogenation is a type of elimination reaction where a hydrogen atom and a halogen atom are removed from a molecule. This process leads to the formation of an alkene product. In the context of our exercise, dehydrohalogenation involves the compound \(\mathrm{C}_7\mathrm{H}_{15}\mathrm{Br}\), where sodium ethoxide in ethanol acts as the base to facilitate this reaction. During dehydrohalogenation:
  • The base abstracts a proton (H\(^+\)) adjacent to the carbon bearing the bromine atom (Br).
  • This results in the formation of a double bond between two carbon atoms.
  • The halogen (bromine in this case) leaves the molecule, completing the process.
This reaction is significant because it transforms the saturated molecule into an unsaturated alkene, specifically forming compounds B and C in the exercise. Understanding dehydrohalogenation helps us predict the types of alkenes that can be formed from different substrates during elimination reactions. **Key Takeaway:** The presence of a good leaving group, like bromine, and a suitable base is critical for dehydrohalogenation to successfully produce alkenes.
Alkene Formation
Alkene formation is the primary outcome of dehydrohalogenation reactions, as seen when compound \(\mathrm{A(C}_7\mathrm{H}_{15}\mathrm{Br})\) is reacted with sodium ethoxide in ethanol. The reaction yields two different alkenes, B and C, both having the molecular formula \(\mathrm{C}_7\mathrm{H}_{14}\), indicating that they are isomers. During the formation of alkenes, the carbon atoms involved in the double bond come together to form the characteristic planar structure of alkenes. The two alkenes here are likely formed through the elimination from different hydrogen atoms along the carbon chain, leading to distinct structural properties while maintaining the same molecular formula. This structural variance can have implications on the physical and chemical properties of the alkenes. **Key Point:** Understanding alkene formation involves recognizing the changes in bond formation, from single bonds in alkanes to double bonds in alkenes, which profoundly affect the geometry and reactivity of the compound.
Isomeric Compounds
Isomeric compounds are molecules that have the same molecular formula but differ in the arrangement of atoms. In our exercise, aldenes B and C both have the molecular formula \(\mathrm{C}_7\mathrm{H}_{14}\). This means they are isomers. Isomerism in alkenes typically arises from different possibilities in:
  • The position of the double bond within the carbon chain.
  • The branching of the carbon chain itself.
These variations lead to different structural isomers like 3-ethyl-1-hexene and 4-ethyl-2-pentene, as identified in the exercise. Both can reduce to the same alkane, 3-ethylpentane, upon hydrogenation, confirming their structural compatibility despite being isomers. **Conclusion:** Recognizing isomeric alkenes helps us understand the diverse chemical behaviors that can happen despite a consistent molecular formula, particularly how they might differ in physical properties or reactivity.
Catalytic Hydrogenation
Catalytic hydrogenation is a process where alkenes are converted back into the corresponding alkanes in the presence of a catalyst, such as palladium, platinum, or nickel. Here, compounds B and C are subject to hydrogenation, and both yield or revert to 3-ethylpentane.The hydrogenation process occurs as follows:
  • Hydrogen gas \(\mathrm{H}_2\) is introduced to the unsaturated alkene.
  • The catalyst facilitates the addition of hydrogen atoms across the double bond.
  • This reduces the double bond to a single bond, thus saturating the alkene into an alkane.
This transformation demonstrates how double bonds in alkenes, like those present in B and C, entirely saturate to form alkanes like 3-ethylpentane. **Final Thoughts:** Catalytic hydrogenation is a crucial reaction in organic chemistry for converting unsaturated compounds into stable saturated structures. This process is valuable in understanding the full scope of reactivity and stability between different types of hydrocarbons.

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Most popular questions from this chapter

A mixture of three alkenes (A, B, and C) was obtained by dehydration of 1,2 dimethylcyclohexanol. The composition of the mixture was A (3\%), B (31\%), and C (66\%). Catalytic hydrogenation of A, B, or C gave 1,2-dimethylcyclohexane. The three alkenes can be equilibrated by heating with sulfuric acid to give a mixture containing \(\mathrm{A}(0 \%), \mathrm{B}(15 \%)\), and \(\mathrm{C}(85 \%)\). Identify \(\mathrm{A}, \mathrm{B}\), and \(\mathrm{C}\).

Write the structure of the major organic product formed in the reaction of 1 -pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{~S}\)

Apply retrosynthetic analysis to guide the preparation of each of the following compounds from the indicated starting material, then write out the synthesis showing the necessary reagents. (a) 1-Propanol from 2-propanol (b) 1,2-Dibromopropane from 2-bromopropane (c) 1-Bromo-2-propanol from 2-propanol (d) 1-Bromo-2-methyl-2-propanol from tert-butyl bromide (e) 1,2-Epoxypropane from 2-propanol (f) tert-Butyl alcohol from isobutyl alcohol (g) tert-Butyl iodide from isobutyl iodide (h) trans-2-Chlorocyclohexanol from cyclohexyl chloride

A certain compound of molecular formula \(\mathrm{C}_{19} \mathrm{H}_{38}\) was isolated from fish oil and from plankton. On hydrogenation it gave \(2,6,10,14\) -tetramethylpentadecane. Ozonolysis gave \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{O}\) and a 16 -carbon aldehyde. What is the structure of the natural product? What is the structure of the aldehyde?

Specify reagents suitable for converting 3 -ethyl-2-pentene to each of the following: (a) 2,3 -Dibromo-3-ethylpentane (d) 3-Ethyl-2-pentanol (b) 3-Chloro-3-ethylpentane (e) 2,3-Epoxy-3-ethylpentane (c) 3-Ethyl-3-pentanol (f) 3-Ethylpentane

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