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,
SN2 reaction is second order
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
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.
The given molecule is prepared by using nucleophilic substitution reaction.
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,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
The sodium tertiary butoxide is acts as a base and it react with methyl bromide gives the corresponding ether product.
The given molecule is prepared by using nucleophilic substitution reaction.
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,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The product of the reaction is given below,
The reaction is given below,
n-butyl bromide undergoes nucleophilic substitution reaction with cyanide (sodium cyanide) gives the corresponding cyanide product.
The given molecule is prepared by using nucleophilic substitution reaction.
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,
SN2 reaction is second order reaction, the rate of the reaction is depending on the both substrate and nucleophiles.
Answer to Problem 45AP
The reaction is given below,
Explanation of Solution
Given information:
The reaction is given below,
The reaction is given below,
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
The given molecule is prepared by using nucleophilic substitution reaction.
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Chapter 11 Solutions
EBK ORGANIC CHEMISTRY
- For each of the following, indicate whether the arrow pushes are valid. Do we break any rules via the arrows? If not, indicate what is incorrect. Hint: Draw the product of the arrow and see if you still have a valid structure. a. b. N OH C. H N + H d. e. f. مه N COHarrow_forwardDecide which is the most acidic proton (H) in the following compounds. Which one can be removed most easily? a) Ha Нь b) Ha Нь c) CI CI Cl Ha Ньarrow_forwardProvide all of the possible resonanse structures for the following compounds. Indicate which is the major contributor when applicable. Show your arrow pushing. a) H+ O: b) c) : N :O : : 0 d) e) Оarrow_forward
- Draw e arrows between the following resonance structures: a) b) : 0: :0: c) :0: N t : 0: بار Narrow_forwardDraw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. Cl Substitution will not occur at a significant rate. Explanation Check :☐ O-CH + Х Click and drag to start drawing a structure.arrow_forwardDraw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. Cl C O Substitution will not occur at a significant rate. Explanation Check + O-CH3 Х Click and drag to start drawing a structure.arrow_forward
- ✓ aw the major substitution products you would expect for the reaction shown below. If substitution would not occur at a significant rate under these conditions, check the box underneath the drawing area instead. Be sure you use wedge and dash bonds where necessary, for example to distinguish between major products. Note for advanced students: you can assume that the reaction mixture is heated mildly, somewhat above room temperature, but strong heat or reflux is not used. C Cl HO–CH O Substitution will not occur at a significant rate. Explanation Check -3 ☐ : + D Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacy Cearrow_forwardPlease correct answer and don't used hand raitingarrow_forwardDon't used hand raiting and don't used Ai solutionarrow_forward
- Determine whether the following reaction is an example of a nucleophilic substitution reaction: Br OH HO 2 -- Molecule A Molecule B + Br 义 ollo 18 Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. Which of the reactants is referred to as the nucleophile in this reaction? Which of the reactants is referred to as the organic substrate in this reaction? Use a ŏ + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. ◇ Yes O No O Molecule A Molecule B Molecule A Molecule B टेarrow_forwardPlease correct answer and don't used hand raitingarrow_forwardPlease correct answer and don't used hand raitingarrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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