Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 11.SE, Problem 50AP

What products would you expect from the reaction of 1-bromopropane with each of the following?

(a) NaNH2

(b) KOC(CH3)3

(c) NaI

(d) NaCN

(e) NaC≡CH

(f) Mg, then H2O

Expert Solution
Check Mark
Interpretation Introduction

a)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  1

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  2

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  3

The sodium amide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.

1-bromo propane undergoes nucleophilic substitution reaction gives propyl amine as a minor product.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

Expert Solution
Check Mark
Interpretation Introduction

b)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  4

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  5

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  6

The potassium tertiary butoxide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

Expert Solution
Check Mark
Interpretation Introduction

c)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  7

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  8

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  9

The sodium iodide is acts as nucleophile, 1-bromo propane undergoes nucleophilic substitution reaction with sodium iodide gives 1-iodo propane.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

Expert Solution
Check Mark
Interpretation Introduction

d)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  10

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  11

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  12

The sodium amide is acts as a base and it abstract the acidic proton from 1-bromo propane gives carbanion, this carbanion under goes elimination reaction gives propene as a major product.

1-bromo propane undergoes nucleophilic substitution reaction gives propyl amine as a minor product.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

Expert Solution
Check Mark
Interpretation Introduction

e)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  13

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  14

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  15

1-bromo propane undergoes nucleophilic substitution reaction with given alkyne compound gives the corresponding alkyne product.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

Expert Solution
Check Mark
Interpretation Introduction

f)

Interpretation:

The product has to be identified when 1-bromopropane reacts with the given reagents.

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 SN1 substitution 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.

Elimination reaction: An elimination reaction is removal of two substituents in a molecule and forms alkene. An elimination reaction is one or two-step process which based on the mechanism when two substituents removed from the molecule in single step is called E2 reaction. When two substituents are removed from the molecule in two steps is called E1 reaction.

The Grignard reaction:

Alkyl, vinyl, or aryl-magnesium halides (RMgX) is called as Grignard reagent.

Answer to Problem 50AP

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  16

Explanation of Solution

Given information:

The reactant of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  17

The product of the reaction is given below,

Organic Chemistry, Chapter 11.SE, Problem 50AP , additional homework tip  18

1-bromo propane reaction with magnesium gives Grignard reagent and it undergoes hydrolysis gives propane.

Conclusion

The product of the reaction is given when 1-bromopropane reacts with the given reagents.

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
Predict the major products (including stereochemistry) when cis-3-methylcyclohexanol reacts with the following reagents. (a) concentrated HBr (b) TsCl/pyridine, then NaBr
Q3: What products would you expect from the reaction of 1-bromopropane with each of the following?(a)NaNH2 (b) KOC(CH3)3 (c) Nal(d) NaCN (e) NaC=CH (f) Mg, then H2O
Identify (A) in the following reaction. 2H2 Pt (A) KMNO4 Warm conc. || С — С — о—н |CO,H + HO CO2H cis-cyclo hexane 1,2-dicarboxylic acid (a) (b) (c) (d)

Chapter 11 Solutions

Organic Chemistry

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
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
Coenzymes and cofactors; Author: CH15 SWAYAM Prabha IIT Madras;https://www.youtube.com/watch?v=bubY2Nm7hVM;License: Standard YouTube License, CC-BY
Aromaticity and Huckel's Rule; Author: Professor Dave Explains;https://www.youtube.com/watch?v=7-BguH4_WBQ;License: Standard Youtube License