Question
Book Icon
Chapter 11.SE, Problem 45AP
Interpretation Introduction

a)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

SN1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.

SN2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  1

SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Expert Solution
Check Mark

Answer to Problem 45AP

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  2

Explanation of Solution

Given information:

The product of the reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  3

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  4

The sodium amide is acts as a base and it abstract the highly acidic proton from propylene gives carbanion, this carbanion react with 2-bromo propane gives the corresponding product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

b)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

SN1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.

SN2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  5

SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Expert Solution
Check Mark

Answer to Problem 45AP

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  6

Explanation of Solution

Given information:

The product of the reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  7

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  8

The sodium tertiary butoxide is acts as a base and it react with methyl bromide gives the corresponding ether product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

c)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

SN1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.

SN2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  9

SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Expert Solution
Check Mark

Answer to Problem 45AP

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  10

Explanation of Solution

Given information:

The product of the reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  11

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  12

n-butyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

Interpretation Introduction

d)

Interpretation:

The given molecule has to be prepared by using nucleophilic substitution reaction.

Concept introduction:

SN1 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid which yield the corresponding carbocation intermediate, this carbocation intermediate undergoes substitution reaction which yields the corresponding substitution product.

Tertiary alcohols undergo substitution very fast than the secondary alcohols because tertiary carbocation is more stable than the secondary carbocation than the primary carbocation.

Primary alcohol is less stable therefore it won’t undergo SN1substitution reaction.

SN2 reaction:

The alcohol is reaction with acids like hydrochloric acid or hydrobromic acid, the bromine atom attacks back side of the carbon atoms in simultaneous manner and which is bearing alcohol group which yield the corresponding product.

Example:

Alcohol is reaction with tosyl chloride in pyridine which provides retention of configuration of tosylated compound. This tosylated compound is further reaction with sodium methoxide which undergoes again SN2 type of reaction, the methoxide ion attacks the carbon atom through the back side and provides Inverse configuration of methoxy compound. This is shown below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  13

SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.

Expert Solution
Check Mark

Answer to Problem 45AP

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  14

Explanation of Solution

Given information:

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  15

The reaction is given below,

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!), Chapter 11.SE, Problem 45AP , additional homework tip  16

Ethyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product, this cyanide undergoes catalytic reduction using Pt (metal reduction) gives amine compound.

Conclusion

The given molecule is prepared by using nucleophilic substitution reaction.

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
81. a. Propose a mechanism for the following reaction: OH CH2=CHCHC=N b. What is the product of the following reaction? HO H₂O N=CCH2CH2CH OH HO CH3CCH=CH2 H₂O C=N 82. Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene a sulfonium ulia
For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? NH2 MgBr Will the first product that forms in this reaction create a new CC bond? ○ Yes ○ No MgBr ? Will the first product that forms in this reaction create a new CC bond? O Yes O No Click and drag to start drawing a structure. :☐ G x c olo Ar HE
Predicting As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will make a molecule with a new C - C bond as its major product: H₂N O H 1. ? 2. H3O+ If this reaction will work, draw the major organic product or products you would expect in the drawing area below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry. 0 If the major products of this reaction won't have a new CC bond, just check the box under the drawing area and leave it blank. فا Explanation Check Click and drag to start drawing a structure.

Chapter 11 Solutions

Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)

Ch. 11.5 - Rank the following substances in order of their...Ch. 11.5 - 3-Bromo-1-butene and 1-bromo-2-butene undergo SN1...Ch. 11.5 - Prob. 13PCh. 11.6 - Review the mechanism of geraniol biosynthesis...Ch. 11.7 - Prob. 15PCh. 11.7 - What alkyl halides might the following alkenes...Ch. 11.8 - Prob. 17PCh. 11.8 - Prob. 18PCh. 11.9 - Prob. 19PCh. 11.12 - Prob. 20PCh. 11.SE - Prob. 21VCCh. 11.SE - From what alkyl bromide was the following alkyl...Ch. 11.SE - Prob. 23VCCh. 11.SE - Prob. 24VCCh. 11.SE - Prob. 25MPCh. 11.SE - Prob. 26MPCh. 11.SE - Prob. 27MPCh. 11.SE - Prob. 28MPCh. 11.SE - Prob. 29MPCh. 11.SE - Prob. 30MPCh. 11.SE - Prob. 31MPCh. 11.SE - Prob. 32MPCh. 11.SE - Metabolism of S-adenosylhomocysteine (Section...Ch. 11.SE - Reaction of iodoethane with CN- yields a small...Ch. 11.SE - One step in the urea cycle for ridding the body of...Ch. 11.SE - Prob. 36MPCh. 11.SE - Prob. 37MPCh. 11.SE - Propose a mechanism for the following reaction, an...Ch. 11.SE - Prob. 39APCh. 11.SE - The following Walden cycle has been carried out....Ch. 11.SE - Prob. 41APCh. 11.SE - Which reactant in each of the following pairs is...Ch. 11.SE - Prob. 43APCh. 11.SE - Prob. 44APCh. 11.SE - Prob. 45APCh. 11.SE - Prob. 46APCh. 11.SE - Prob. 47APCh. 11.SE - Prob. 48APCh. 11.SE - Propose structures for compounds that fit the...Ch. 11.SE - What products would you expect from the reaction...Ch. 11.SE - Prob. 51APCh. 11.SE - Prob. 52APCh. 11.SE - Prob. 53APCh. 11.SE - Prob. 54APCh. 11.SE - Prob. 55APCh. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Order each of the following sets of compounds with...Ch. 11.SE - Prob. 58APCh. 11.SE - Prob. 59APCh. 11.SE - Ethers can often be prepared by SN2 reaction of...Ch. 11.SE - Show the stereochemistry of the epoxide (see...Ch. 11.SE - Prob. 62APCh. 11.SE - In addition to not undergoing substitution...Ch. 11.SE - The tosylate of (2R, 3S)-3-phenyl-2-butanol...Ch. 11.SE - Prob. 65APCh. 11.SE - Prob. 66APCh. 11.SE - Prob. 67APCh. 11.SE - Prob. 68APCh. 11.SE - Prob. 69APCh. 11.SE - (S)-2-Butanol slowly racemizes on standing in...Ch. 11.SE - Reaction of HBr with (R)-3-methyl-3-hexanol leads...Ch. 11.SE - Treatment of 1-bromo-2-deuterio-2-phenylethane...Ch. 11.SE - Prob. 73APCh. 11.SE - Prob. 74APCh. 11.SE - In light of your answer to Problem 11-74, explain...Ch. 11.SE - Prob. 76APCh. 11.SE - Compound X is optically inactive and has the...Ch. 11.SE - When a primary alcohol is treated with...Ch. 11.SE - Prob. 79APCh. 11.SE - Amines are converted into alkenes by a two-step...Ch. 11.SE - The antipsychotic drug flupentixol is prepared by...
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning