Draw a structural formula for the major organic product of each reaction and specify the most likely mechanism by which each is formed.
(g)
(a)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
Methanol is a polar protic solvent, moderate nucleophile and alkyl halide forms allyl cation, it is stable cation.
Hence, the given reaction is takes place in both
(b)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a tertiary halide, sodium hydroxide is strong base and water is polar solvent hence, the given reaction is takes place in
(c)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a secondary halide, sodium acetate is strong neucleophile and DMSO is polar aprotic solvent hence, the given reaction is takes place in
(d)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a secondary halide, sodium methoxide is strong base and methonal is polar solvent hence, the given reaction is takes place in
(e)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a secondary halide, iodide is strong nucleophile and acetone is polar solvent hence, the given reaction is takes place in
(f)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a secondary halide, formic acid is moderate nucleophile and is polar solvent hence, the given reaction is takes place in both
(g)
Interpretation:
The structural formula for the major organic product has to be drawn and mechanism of the given reaction has to be specified.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Elimination:
An atom or group are removed from saturated compound to give unsaturated alkene is known as elimination reaction.
In elimination, the removal of halogen ion forms a carbocation followed by removal of hydrogen ion forms an alkene is known as E1 reaction.
The abstraction of proton and removal of leaving group takes simultaneously means it is E2 reaction because the rate of reaction depends on both base and substrate.
E1 elimination fallows saytzeff rule (more substituted alkene is formed).
Explanation of Solution
The given alkyl halide is a allyl halide, sodium ethoxide is strong base and ethanol is polar solvent hence, the given reaction is takes place in
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Chapter 9 Solutions
Organic Chemistry
- The rate of hydration of 2-butene and 2-methylpropene differ by several orders of magnitude. Please state which alkene is more rapidly hydrated and why.arrow_forwardWrite down the common (not IUPAC) names of the organic molecules that would be released if this molecule were hydrolyzed: CH,—O—C—(CH2)—CH=CH-CH,—CH=CH—(CH2) — CH3 CH-0- -(CH2)–CH=CH(CH2)CH3 O CH,—O-C=(CH2)=CH=CH(CH2)—CH3 Separate each name with a comma and a space. You will find useful information in the ALEKS Data resource. type your answer...arrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below.CH3CH3+ Cl2→ CH3CH2Cl+ HClDescribe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forward
- Write down the common (not IUPAC) names of the organic molecules that would be released if this molecule were hydrolyzed: о CH2 O-C-(CH2)7-CH=CH-CH2-CH=CH-(CH2)4-CH3 о CH-O-C-(CH2)7-CH=CH-CH2-CH=CH-CH2-CH=CH-CH2-CH3 CH2 O-C-(CH2)4-CH=CH-CH2-CH=CH-CH2-CH=CH-(CH2)4-CH3 Separate each name with a comma. You will find useful information in the ALEKS Data resource.arrow_forward5A In the following reactions, mixtures of alkenes and ethyl ethers are formed. Draw their structures. Explain which is or are likely to be the main product(s) in each reaction. In case of formation of two isomers of alkenes, explain which is formed in greater proportion CH3 ofi H3C- -Br CH3 EtOHarrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes placearrow_forward
- Ethane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish.arrow_forwardEthane reacts with chlorine (Cl2) in the presence of ultra-violet (UV) light, to produce 1-chloropropane (CH3CH2Cl) and hydrogen bromide (HCl). As shown in the equation below. CH3CH3 + Cl2 → CH3CH2Cl + HCl Describe the reaction mechanism of the reaction between ethane and chlorine to produce 1-chloroethane. The description should be detailed and must include the type of bond fission that takes place. You may sketch and insert suitable diagrams to aid your description if you wish. Would this reaction (question 34(c)) give a high yield of 1-chloroethanearrow_forwardWrite down the common (not IUPAC) names of the organic molecules that would be released if this molecule were hydrolyzed: о CH2-0-C-(CH2)7-CH=CH-CH2-CH=CH-(CH2)4-CH3 CH о O-C-(CH2)7-CH=CH-CH2-CH=CH-CH2-CH=CH-CH2-CH3 CH2-O-C-(CH2)4-CH=CH-CH2-CH=CH-CH2-CH=CH-(CH2)4-CH3 Separate each name with a comma. You will find useful information in the ALEKS Data resource.arrow_forward
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardCH3COOH + 2H2 = C2H5OH + H2O %3D Acetate Ethanol Acetate may be hydrogenated to ethanol in industrial reaction systems using several catalysts: Select the most effective catalyst for this reaction system if the free energy of the reaction is -34 kJ/mol; Catalist effective at the temperature range 37-45°C, O Catalist effective at the temperature range 40-55°C, O Catalist effective at the temperature range 60-72°C,arrow_forwardAcid-catalyzed dehydration of secondary and tertiary alcohols proceeds through an E1 mechanism. The first step is the protonation of the alcohol oxygen to form an oxonium ion. Dehydration of 3-methyl-2-butanol forms one major and two minor organic products. Draw the structures, including hydrogen atoms, of the three organic products of this reaction. н н :бн н Нас. Нас. CHз CH3 ČH3 CH3 3-methyl-2-butanol an oxonium ion Major Product Minor Product Minor Productarrow_forward