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

Interpretation Introduction

a)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.

Interpretation Introduction

b)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.

Interpretation Introduction

c)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.

Interpretation Introduction

d)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.

Interpretation Introduction

e)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.

Interpretation Introduction

f)

Interpretation:

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

Concept introduction:

S_N1 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 S_N1 substitution reaction.

S_N2 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,

Explanation of Solution

Given information:

The reactant of the reaction is given below,

The product of the reaction is given below,

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.