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Chapter 11: Problem 19

Draw the structure and give the systematic name for the products of the following reactions: (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CH}_{2}+\mathrm{Br}_{2} \longrightarrow\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{CHCH}_{3}+\mathrm{H}_{2} \longrightarrow\)

Short Answer

Expert verified
(a) 1,2-dibromopropane; (b) pentane.

Step by step solution

01

Understand Reaction (a)

In reaction (a), propene \( \mathrm{CH}_3 \mathrm{CH} = \mathrm{CH}_2 \) is reacting with bromine \( \mathrm{Br}_2 \). This is an addition reaction where bromine will add across the double bond.
02

Predict the Product for (a)

The double bond between the second and third carbon will break and each carbon involved in the double bond will bond with a bromine atom. The structure becomes \( \mathrm{CH}_3 \mathrm{CHBrCH}_2\mathrm{Br} \), which is called 1,2-dibromopropane.
03

Understand Reaction (b)

In reaction (b), 2-pentene \( \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH} = \mathrm{CHCH}_3 \) is reacting with hydrogen \( \mathrm{H}_2 \). This is a hydrogenation reaction which will saturate the molecule by converting the double bond into a single bond, adding hydrogen atoms.
04

Predict the Product for (b)

During hydrogenation, one hydrogen atom will add to each carbon that was previously double-bonded. The structure becomes \( \mathrm{CH}_3\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_2\mathrm{CH}_3 \), which is called pentane.

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Key Concepts

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

Addition Reactions
Addition reactions are a fundamental type of reaction in organic chemistry. These reactions involve the addition of atoms or groups of atoms to a molecule, typically across a double bond or triple bond. In an addition reaction:
  • The pi bond (double or triple bond) between two carbon atoms is broken, resulting in two new sigma bonds.
  • This usually increases the saturation of the molecule, transforming unsaturated compounds into saturated ones.
  • The two new atoms or groups are added to each carbon atom that was previously part of the double or triple bond.
Addition reactions are important because they allow chemists to systematically modify carbon skeletons, introducing new functional groups and building complexity in organic molecules.
Bromination
Bromination is a specific type of addition reaction where bromine (Br鈧�) is added to compounds containing double or triple bonds. This typically involves:
  • The bromine molecule approaching the carbon-carbon double bond.
  • Breaking of the pi bond upon interaction, which allows each carbon atom to form a new bond with a bromine atom.
  • Formation of a colorless dibromide product from the initially colored bromine solution, indicating the reaction has occurred.
In reaction (a) from our exercise, bromination was used on propene (an alkene), resulting in the formation of 1,2-dibromopropane. Bromination reactions serve as a simple test for unsaturation, as alkenes and alkynes decolorize bromine water.
Hydrogenation
Hydrogenation is a vital reaction in organic chemistry, transforming unsaturated molecules, such as alkenes and alkynes, into saturated alkanes. The key aspects of hydrogenation include:
  • Addition of hydrogen (H鈧�) across a double or triple bond.
  • Use of a catalyst, often platinum, palladium, or nickel, to facilitate the reaction by lowering the activation energy.
  • Saturation of the molecule, as hydrogen atoms break the double bonds, converting them into single bonds.
In the context of our exercise, hydrogenation was applied to 2-pentene, converting it into pentane. Hydrogenation is practical in industries for processes such as the hardening of fats and oils.
Propene
Propene, also known as propylene, is a simple alkene with the molecular formula C鈧僅鈧�. It features:
  • A three-carbon chain with a single double bond between the first and second carbon atoms.
  • Being a typical example of a small industrial alkene used for making plastics and chemicals.
  • A reactive nature due to its double bond, making it a major candidate for addition reactions like bromination and hydrogenation.
In the given exercise, propene undergoes bromination, illustrating its role as a reactant that can easily participate in addition reactions to form more complex compounds.
2-Pentene
2-Pentene is a type of alkene with the formula C鈧匟鈧佲個. It is characterized by:
  • A five-carbon chain with a double bond between the second and third carbon atoms, distinguishing it from its isomer 1-pentene.
  • Being part of the pentene family, which are used as intermediates in chemical syntheses.
  • Having geometric isomers (cis and trans forms) due to the restricted rotation around the double bond.
In our exercise, 2-pentene is the compound subject to hydrogenation, resulting in the fully saturated alkane, pentane. Understanding its structure and reactivity assists with grasping how hydrogenation eliminates unsaturation in alkenes.

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Most popular questions from this chapter

You are asked to identify an unknown colorless, liquid carbonyl compound. Analysis has determined that the formula for this unknown is \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O} .\) Only two compounds match this formula. (a) Draw structures for the two possible compounds. (b) To decide which of the two structures is correct, you react the compound with an oxidizing agent, and isolate from that reaction a compound that is found to give an acidic solution in water. Use this result to identify the structure of the unknown. (c) Name the acid formed by oxidation of the unknown.

Give structural formulas and systematic names for possible isomers of dichlorobenzene, \(\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{Cl}_{2}\)

Write equations for the following reactions, representing the reactants and products using structural formulas. (a) the hydrolysis of the amide, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONHCH}_{3}\) to form benzoic acid and methylamine (b) the hydrolysis of nylon-66, \(\left[-\mathrm{CO}\left(\mathrm{CH}_{2}\right)_{4} \mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{6} \mathrm{NH}-\right]_{x}\) a polyamide, to give a carboxylic acid and an amine

Write equations for the following reactions, representing the reactants and products using structural formulas. (a) the reaction of acetic acid and sodium hydroxide (b) the reaction of methylamine with \(\mathrm{HCl}\)

Five alkenes have the formula \(\mathrm{C}_{7} \mathrm{H}_{14}\) and a seven- carbon chain. Draw their structures and name them.
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