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
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- Write the systematic name of each organic molecule: structure HO-C-CH2-CH3 O -OH CH3-CH2-CH2-CH2-CH2-C-OH CH3 CH3-CH-CH2-C-OH Explanation Check S namearrow_forwardtheres 2 productsarrow_forwardDraw the major product of this solvolysis reaction. Ignore any inorganic byproducts. + CH3CH2OH Drawing Q Atoms, Bonds and Rings OCH2CH3 || OEt Charges OH 00-> | Undo Reset | Br Remove Done Drag To Pan +arrow_forward
- Draw the major product of this SN1 reaction. Ignore any inorganic byproducts. CH3CO2Na CH3CO2H Drawing + Br Q Atoms, Bonds and Rings OAC Charges OH ОАс Na ဂ Br Undo Reset Remove Done Drag To Pan +arrow_forwardOrganic Functional Groups entifying positions labeled with Greek letters in acids and derivatives 1/5 ssible, replace an H atom on the a carbon of the molecule in the drawing area with a ce an H atom on the ẞ carbon with a hydroxyl group substituent. ne of the substituents can't be added for any reason, just don't add it. If neither substi er the drawing area. O H OH Oneither substituent can be added. Check D 1 Accessibility ado na witharrow_forwardDifferentiate between electrophilic and nucleophilic groups. Give examples.arrow_forward
- An aldehyde/ketone plus an alcohol gives a hemiacetal, and an excess of alcohol gives an acetal. The reaction is an equilibrium; in aldehydes, it's shifted to the right and in ketones, to the left. Explain.arrow_forwardDraw a Haworth projection or a common cyclic form of this monosaccharide: H- -OH H- OH H- -OH CH₂OHarrow_forwardAnswer the question in the first photoarrow_forward
- Ggggffg2258555426855 please don't use AI Calculate the positions at which the probability of a particle in a one-dimensional box is maximum if the particle is in the fifth energy level and in the eighth energy level.arrow_forwardExplain the concepts of hemiacetal and acetal.arrow_forwardBriefly describe a nucleophilic addition.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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