BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)
8th Edition
ISBN: 9781337687539
Author: Brown/Iverson/Anslyn/ Foote
Publisher: CENGAGE C
bartleby

Videos

Textbook Question
Book Icon
Chapter 6, Problem 6.17P

Predict the organic product(s) of the reaction of 2-butene with each reagent.

  1. (a) H2O (H2SO4)
  2. (b) Br2
  3. (c) Cl2
  4. (d) Br2 in H2O
  5. (e) HI
  6. (f) Cl2 in H2O
  7. (g) Hg(OAc)2, H2O
  8. (h) product (g) 1 NaBH4

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Carbocation: carbon atom bears positive charged species with three bonds is called Carbocation and it plays vital intermediate in organic synthesis. Carbocation migratory aptitude is mainly depends on the stability of the carbocation. This type of carbocation undergoes inter or intra molecule reactions and it form more stable product this type of rearrangement called carbocation rearrangement.

Carbocation’s are classified in to three types as primary, secondary and tertiary depending on the number of carbon atoms which is attached to the ionized carbon.

Tertiary carbocation is more stable than secondary carbocation, secondary carbocation is more stable than the primary carbocation as shown below.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  1

Hydration:

When alkene is undergoes hydration with water in the presence of sulfuric acid which yields the alcohol. In this reaction, the water molecule will behave like a hydrogen halide to the alkene which gives the addition product this reaction is known as a hydration reaction.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  2

Alkene is reaction with water in the presence of sulfuric acid, first step is proton (H+) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (-OH) yields alcohol as a product. The stability of carbocation is given below, Tertiary carbocation is more stable than the secondary, secondary carbocation is more stable than primary.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  3

In hydration reaction, sulfuric acid is act as a proton donor, which is the driving force of the reaction. Hydration reaction will not go without acid (sulfuric acid).

Explanation of Solution

2-Butene reacts with water in the presence of sulfuric acid, first step is proton (H+) addition to the double bond which forms carbocation (more stable carbocation) followed by addition of hydroxide ion (-OH) yields alcohol as a product A. The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  4

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Bromination of alkenes:

Alkene undergoes bromination which yields the dibromo compound (vicinal dibromides or 1,2-dibromides).

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  5

Explanation of Solution

2-Butene undergoes bromination which yields the dibromo compound (B, vicinal dibromides or 1,2-dibromides). The addition product is a chiral molecule, it has two chiral center. Three stereoisomers are possible namely meso compound and stereoisomer.

The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  6

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Chlorination of alkenes:

Alkene undergoes chlorination which yields the dichoro compound (vicinal dichlorides or 1,2-dichlorides).

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  7

Explanation of Solution

2-Butene undergoes chlorination which yields the dichoro compound (A, vicinal dichlorides or 1,2-dichlorides). The addition product is a chiral molecule, it has two chiral center. Three stereoisomers are possible namely meso compound and stereoisomer.

The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  8

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Alkenes reaction with halogens (bromine, chlorine) in the presence of water which gives three membered ring intermediate, this three membered ring intermediate is highly reactive and it is reaction with hydroxide ion which produces chloro hydrine or bromo hydrine derivative.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  9

Explanation of Solution

2-Butene reacts with bromine in the presence of water which gives three membered ring intermediate, this three membered ring intermediate is highly reactive and it is reaction with hydroxide ion (from water) which produces bromo hydrine derivative. The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  10

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Carbocation: carbon atom bears positive charged species with three bonds is called Carbocation and it plays vital intermediate in organic synthesis. Carbocation migratory aptitude is mainly depends on the stability of the carbocation. This type of carbocation undergoes inter or intra molecule reactions and it form more stable product this type of rearrangement called carbocation rearrangement.

Carbocation’s are classified in to three types as primary, secondary and tertiary depending on the number of carbon atoms which is attached to the ionized carbon.

Tertiary carbocation is more stable than secondary carbocation, secondary carbocation is more stable than the primary carbocation as shown below.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  11

Markovnikov’s rule: unsymmetrical alkene reacts with hydrogen halide, halide ions goes to the more substitution position of carbon-carbon double bond which provides alkyl halides.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  12

Explanation of Solution

The 2-butene reacts with hydrogen iodide forms carbocation intermediate, then iodine ion reacts with carbocation yields addition product B. Tertiary carbocation is more stable than secondary carbocation, secondary carbocation is more stable than the primary carbocation.

The addition product is a chiral molecule, it has one chiral center. The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  13

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Alkenes reaction with halogens (bromine, chlorine) in the presence of water which gives three membered ring intermediate, this three membered ring intermediate is highly reactive and it is reaction with hydroxide ion which produces chloro hydrine or bromo hydrine derivative.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  14

Explanation of Solution

2-Butene reacts with chlorine in the presence of water which gives three membered ring intermediate, this three membered ring intermediate is highly reactive and it is reaction with hydroxide ion (from water) which produces chloro hydrine derivative. The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  15

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Oxymercuration:

Alkenes reaction with mercuric acetate in the presence of water, the HgOAc adds to the less substituted carbon on carbon – carbon double bond and gives the corresponding organomercuric compound.

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  16

Explanation of Solution

2-Butene reacts reaction with mercuric acetate in the presence of water, the HgOAc additon to the less substituted carbon on carbon – carbon double bond and gives the corresponding organomercuric compound. The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  17

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The product of the reaction has to be predicted.

Concept interpretation:

Oxymercuration:

Alkenes reaction with mercuric acetate in the presence of water, the HgOAc adds to the less substituted carbon on carbon – carbon double bond and gives the corresponding organomercuric compound. It undergoes reduction using sodium borohydride gives corresponding alcohol (B)

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  18

Explanation of Solution

2-Butene reacts reaction with mercuric acetate in the presence of water, the HgOAc additon to the less substituted carbon on carbon – carbon double bond and gives the corresponding organomercuric compound. It undergoes reduction using sodium borohydride gives corresponding alcohol (B).

The reaction is shown below,

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD), Chapter 6, Problem 6.17P , additional homework tip  19

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
8
(d) When butane, CH3CH2CH2CH3 and bromine gas, Br2 is exposed to sunlight, monobrominated product are produced. The reaction equation is given below: uv CH;CH,CH,CH3 + Br2 A + B (i) State the type of reaction. (ii) What is the function of the sunlight in the reaction? (iii) Draw the structure of monosubstituted products, A and B. Label the major product. (iv) Draw the propagation steps in the mechanism for the formation of the major product.
Starting from bromoethane, the formation of which of the following compound requires more than one step of reaction? 2 (a) Methoxyethane (b) Ethanol (c) Ethanoic acid (d) Ethene

Chapter 6 Solutions

BNDL: ACP ORGANIC CHEMISTRY:CH EM 231(W/ACCESS CARD)

Ch. 6.5 - Prob. 6.11PCh. 6.5 - Prob. 6.12PCh. 6.5 - What alkene with the molecular formula C6H12, when...Ch. 6 - Prob. 6.15PCh. 6 - Prob. 6.16PCh. 6 - Predict the organic product(s) of the reaction of...Ch. 6 - Prob. 6.18PCh. 6 - Prob. 6.20PCh. 6 - Draw a structural formula for an alkene with the...Ch. 6 - Account for the fact that addition of HCl to...Ch. 6 - Account for the fact that treating propenoic acid...Ch. 6 - Draw a structural formula for the alkene with the...Ch. 6 - Draw the alternative chair conformations for the...Ch. 6 - Draw a structural formula for the cycloalkene with...Ch. 6 - Reaction of this bicycloalkene with bromine in...Ch. 6 - Terpin, prepared commercially by the...Ch. 6 - Propose a mechanism for this reaction and account...Ch. 6 - Treating 2-methylpropene with methanol in the...Ch. 6 - When 2-pentene is treated with Cl2 in methanol,...Ch. 6 - Treating cyclohexene with HBr in the presence of...Ch. 6 - Propose a mechanism for this reaction. 1-Pentane...Ch. 6 - Treating 4-penten-1-ol with bromine in water forms...Ch. 6 - Prob. 6.35PCh. 6 - Prob. 6.36PCh. 6 - Reaction of -pinene with borane followed by...Ch. 6 - Write structural formulas for the major organic...Ch. 6 - Draw the structural formula of the alkene that...Ch. 6 - Consider the following reaction. (a) Draw a...Ch. 6 - Prob. 6.42PCh. 6 - Prob. 6.43PCh. 6 - Show how to convert ethylene to these compounds....Ch. 6 - Show how to convert cyclopentene into these...Ch. 6 - Prob. 6.46PCh. 6 - Describe the stereochemistry of the bromohydrin...Ch. 6 - Prob. 6.49PCh. 6 - Treating 1,3-butadiene with 1 mole of HBr gives a...Ch. 6 - In this chapter, we studied the mechanism of the...Ch. 6 - As we have seen in this chapter, carbon-carbon...Ch. 6 - Prob. 6.53PCh. 6 - Prob. 6.54P
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
07 Physical Properties of Organic Compounds; Author: Mindset;https://www.youtube.com/watch?v=UjlSgwq4w6U;License: Standard YouTube License, CC-BY