/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Problem 33 Write a chemical equation for th... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 5: Problem 33

Write a chemical equation for the reaction of 1 -butanol with each of the following: (a) Sodium amide \(\left(\mathrm{NaNH}_{2}\right)\) (d) Phosphorus tribromide (b) Hydrogen bromide, heat (e) Thionyl chloride (c) Sodium bromide, sulfuric acid, heat (f) Methanesulfonyl chloride, pyridine

Short Answer

Expert verified
Each reaction converts 1-butanol into different products based on the reagents: alkoxide ion, 1-bromo/chloro derivatives, and methanesulfonate ester.

Step by step solution

01

Understanding the Reaction with Sodium Amide

When 1-butanol reacts with sodium amide \(\mathrm{NaNH}_2\), it undergoes a deprotonation reaction at the hydroxyl group. Sodium amide, being a strong base, abstracts the proton to form the alkoxide ion. The chemical equation can be written as: \[\mathrm{C_4H_9OH} + \mathrm{NaNH_2} \rightarrow \mathrm{C_4H_9ONa} + \mathrm{NH_3}\]
02

Reaction with Phosphorus Tribromide

1-butanol reacts with phosphorus tribromide \(\mathrm{PBr_3}\) to form 1-bromobutane and phosphorous acid. This is a substitution reaction where the hydroxyl group is replaced with a bromide ion: \[3\mathrm{C_4H_9OH} + \mathrm{PBr_3} \rightarrow 3\mathrm{C_4H_9Br} + \mathrm{H_3PO_3}\]
03

Reaction with Hydrogen Bromide and Heat

The reaction of 1-butanol with hydrogen bromide (HBr) in the presence of heat leads to the substitution of the hydroxyl group with a bromide ion, producing 1-bromobutane: \[\mathrm{C_4H_9OH} + \mathrm{HBr} \rightarrow \mathrm{C_4H_9Br} + \mathrm{H_2O}\]
04

Reaction with Sodium Bromide, Sulfuric Acid, and Heat

This reaction is an example of a conversion through Halogen Acid (HX) generated in-situ. Sulfuric acid and sodium bromide with heat cause 1-butanol to form 1-bromobutane: \[\mathrm{C_4H_9OH} + \mathrm{NaBr} + \mathrm{H_2SO_4} \rightarrow \mathrm{C_4H_9Br} + \mathrm{NaHSO_4} + \mathrm{H_2O}\]
05

Reaction with Thionyl Chloride

1-butanol reacts with thionyl chloride \(\mathrm{SOCl_2}\) in the presence of a base to substitute the hydroxyl group with a chloride ion, forming 1-chlorobutane: \[\mathrm{C_4H_9OH} + \mathrm{SOCl_2} \rightarrow \mathrm{C_4H_9Cl} + \mathrm{SO_2} + \mathrm{HCl}\]
06

Reaction with Methanesulfonyl Chloride and Pyridine

1-butanol reacts with methanesulfonyl chloride (MsCl) and pyridine (a base) to form butyl methanesulfonate. The hydroxyl group is converted into a better leaving group (methanesulfonate ester): \[\mathrm{C_4H_9OH} + \mathrm{CH_3SO_2Cl} \xrightarrow{\text{pyridine}} \mathrm{C_4H_9OSO_2CH_3} + \mathrm{HCl}\]

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

Key Concepts

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

1-Butanol Reactions
1-Butanol is an alcohol with the chemical formula \(\text{C}_4\text{H}_9\text{OH}\). It is often used in organic chemistry to explore a range of chemical reactions. These reactions typically pass through different pathways, producing various useful products. Here, we focus on how 1-butanol reacts with specific reagents to illustrate the diverse chemical transformations it can undergo.
  • With sodium amide \( (\text{NaNH}_2) \), 1-butanol goes through a deprotonation reaction (removal of a hydrogen atom) to form an alkoxide ion, 1-butoxide \( (\text{C}_4\text{H}_9\text{O}^- \text{Na}^+) \).
  • In a reaction with hydrogen bromide \((\text{HBr})\), the hydroxyl group in 1-butanol is substituted with a bromide ion, creating 1-bromobutane.
  • Phosphorus tribromide \((\text{PBr}_3)\) also converts 1-butanol to 1-bromobutane, while simultaneously generating phosphorous acid \((\text{H}_3\text{PO}_3)\).
Understanding these reactions sheds light on how specific reagents influence the outcome of chemical processes, thereby broadening our knowledge of organic synthesis.
Substitution Reactions
Substitution reactions are a common type of transformation in organic chemistry, where one functional group in a molecule is replaced with another. This type of reaction is essential for modifying molecules into desired derivatives.In the case of 1-butanol, substitution reactions often target the hydroxyl group (\(-OH\)) of the alcohol. Here are some key examples:
  • When 1-butanol reacts with phosphorus tribromide \((\text{PBr}_3)\), the hydroxyl group is replaced by a bromide ion to yield 1-bromobutane. This reaction needs to convert all three hydroxyl groups in three molecules of 1-butanol.
  • Reacting with thionyl chloride \((\text{SOCl}_2)\), the hydroxyl group is replaced by a chloride ion, resulting in 1-chlorobutane. This reaction is useful for creating alkyl chlorides, which are important in various chemical syntheses.
  • In the presence of hydrogen bromide \((\text{HBr})\) and heat, the hydroxyl group is similarly substituted with a bromide ion to form 1-bromobutane.
Substitution reactions are vital for altering the chemical properties of molecules, allowing chemists to create a wide variety of analogs and derivatives.
Deprotonation Reaction
Deprotonation is an essential reaction in organic chemistry where a base removes a proton (\(\text{H}^+\)) from a molecule, often forming an anion. This reaction is crucial for forming intermediates that can further participate in additional chemical transformations.For 1-butanol, the deprotonation reaction occurs when it interacts with sodium amide \((\text{NaNH}_2)\). Sodium amide is a strong base, which makes it effective at removing hydrogen from the hydroxyl group:
  • During this reaction, sodium amide abstracts a proton from the hydroxyl group of 1-butanol.
  • This results in the formation of an alkoxide ion \((\text{C}_4\text{H}_9\text{O}^-\)), combined with sodium to form sodium butoxide.
  • Ammonia \((\text{NH}_3)\) is produced as a byproduct.
The resulting alkoxide ion is highly reactive and can take part in further reactions, offering a pathway for synthesizing different organic compounds.
Chemical Equations
Chemical equations are symbolic representations of chemical reactions. They offer a concise way to display the reactants, products, and their quantities involved in the reaction.Using 1-butanol reactions as examples, chemical equations clearly illustrate the changes that occur:
  • For its reaction with phosphorus tribromide, the equation \(3\mathrm{C_4H_9OH} + \mathrm{PBr_3} \rightarrow 3\mathrm{C_4H_9Br} + \mathrm{H_3PO_3}\) shows three molecules of 1-butanol forming 1-bromobutane and phosphorous acid.
  • The reaction with sodium amide is presented as \(\mathrm{C_4H_9OH} + \mathrm{NaNH_2} \rightarrow \mathrm{C_4H_9ONa} + \mathrm{NH_3}\), illustrating the deprotonation process.
  • Using thionyl chloride, the equation \(\mathrm{C_4H_9OH} + \mathrm{SOCl_2} \rightarrow \mathrm{C_4H_9Cl} + \mathrm{SO_2} + \mathrm{HCl}\) outlines the substitution of a hydroxyl group.
With these visual tools, one can effectively understand how reactants are transformed into products, aiding both learning and teaching in organic chemistry.

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

A hydroxyl group is a somewhat "smaller" substituent on a six-membered ring than is a methyl group. That is, the preference of a hydroxyl group for the equatorial orientation is less pronounced than that of a methyl group. Given this information, write structural formulas for all the isomeric methylcyclohexanols, showing each one in its most stable conformation. Give the substitutive IUPAC name for each isomer.

For the reaction of a primary alcohol \(\mathrm{RCH}_{2} \mathrm{OH}\) with thionyl chloride in pyridine, use curved arrows to show how the last intermediate can be transformed to \(\mathrm{RCH}_{2} \mathrm{Cl}\) by reacting with chloride ion in a single step. Two additional compounds are formed. What are they?

Each of the following is a functional class name developed according to the 1993 IUPAC recommendations. Alkyl group names of this type are derived by naming the longest continuous chain that includes the point of attachment, numbering in the direction so as to give the substituted carbon the lower number. The - \(e\) ending of the corresponding alkane is replaced by \(-y l\), which is preceded by the number corresponding to the substituted carbon bracketed by hyphens. Write a structural formula for each alkyl halide. (a) 6-Methylheptan-3-yl chloride (b) 2,2 -Dimethylpentan- 3 -yl bromide (c) 3,3 -Dimethylcyclopentan-1-yl alcohol

Write structural formulas for all the constitutionally isomeric alcohols of molecular formula \(\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}\). Assign a substitutive and a functional class name to each one, and specify whether it is a primary, secondary, or tertiary alcohol.

\(n\) -Butyl mercaptan is the common name of a foul-smelling substance obtained from skunk spray. It is a thiol of the type \(\mathrm{RX}\), where \(\mathrm{R}\) is an \(n\) -butyl group and \(\mathrm{X}\) is the functional group that characterizes a thiol. Write a structural formula for this substance.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Chemistry Branches

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Nuclear Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.