(a)
To draw: The possible monochlorinated products from the given free-radical chlorination of indane.
Interpretation: The possible monochlorinated products from the given free-radical chlorination of indane are to be drawn.
Concept introduction: The reaction that includes the addition of one or more than one chlorine atoms in a compound is known as chlorination reaction. Chlorination reaction is a type of halogenation reaction.
The free-radical chlorination occurs under the application of UV light on an
Halogenation proceeds via radical substitution reaction because a halogen atom replaces hydrogen through radical mechanism that involves radical intermediates.
(b)
To draw: The possible dichlorinated products from the given free-radical chlorination of indane.
Interpretation: The possible dichlorinated products from the given free-radical chlorination of indane are to be drawn.
Concept introduction: The reaction that includes the addition of one or more than one chlorine atoms in a compound is known as chlorination reaction. Chlorination reaction is a type of halogenation reaction.
The free-radical chlorination occurs under the application of UV light on an alkane compound or he alkyl-substituted aromatic compounds. This reaction proceeds via free-radical chain mechanism.
Halogenation proceeds via radical substitution reaction because a halogen atom replaces hydrogen through radical mechanism that involves radical intermediates.
(c)
To determine: The instrumental technique that is helpful in predicting the total number of products, total number of monochlorinated and dichlorinated products formed by the free-radical chlorination of indane.
Interpretation: The instrumental technique that is helpful in predicting the total number of products, total number of monochlorinated and dichlorinated products formed by the free-radical chlorination of indane is to be predicted.
Concept introduction: The reaction that includes the addition of one or more than one chlorine atoms in a compound is known as chlorination reaction. Chlorination reaction is a type of halogenation reaction.
The free-radical chlorination occurs under the application of UV light on an alkane compound or he alkyl-substituted aromatic compounds. This reaction proceeds via free-radical chain mechanism.
Halogenation proceeds via radical substitution reaction because a halogen atom replaces hydrogen through radical mechanism that involves radical intermediates.
(d)
To determine: The instrumental technique that is useful in detecting the structures of all the dichlorinated products.
Interpretation: The instrumental technique that is useful in detecting the structures of all the dichlorinated products is to be predicted.
Concept introduction: The reaction that includes the addition of one or more than one chlorine atoms in a compound is known as chlorination reaction. Chlorination reaction is a type of halogenation reaction.
The free-radical chlorination occurs under the application of UV light on an alkane compound or he alkyl-substituted aromatic compounds. This reaction proceeds via free-radical chain mechanism.
Halogenation proceeds via radical substitution reaction because a halogen atom replaces hydrogen through radical mechanism that involves radical intermediates.
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Chapter 17 Solutions
Organic Chemistry (9th Edition)
- Item 2 Draw the organic products formed in each reaction. Consider both substitution and elimination products, if possible. Indicate the type of reaction that happened (SN1, SN2, E1, E2). Include stereochemistry and regiochemistry if relevant. For multiple products, identify which is the major and which is th]e minor product. a. b. C. d. e. H₂C 9H **** CH3 CH₂CH3 Br Br CH₂CH C6H5 Br -OC(CH3)3 OC(CH3)3 CH3CH₂OH TOH CH₂OHarrow_forwarda. What is the major monobromination product of the following reaction? Disregard stereoisomers. b. What is the anticipated percent yield of the major product (as a percentage of all the monobrominated products)?arrow_forward3. Which experimental conditions would maximize the yield of choloroethane and minimize the production of polychlorinated products during the free radical chlorination of ethane? A. equimolar amounts of chlorine & ethane C. excess of ethane B. use an excess of chlorine D. excess of chlorine & long reaction time E. equimolar amounts of chlorine & ethane and high reaction temperature 4. How many different dichlorinated propane constitutional isomers are possible ? A. 3 B. 4 C. 5 D. 6 E. 7 5. Which of these steps is most responsible for the tertiary selectivity of free radical bromination of alkanes? A. initiation B. termination C. ionization D. hydrogen abstraction E. halogen abstraction 6. Which radical is most stable? A. CH₂CH₂CH₂CH3 C. CH₂CHCHCH3 D. CH₂CH₂CHCH₂ B. CHCHCH₂CH3 E. CH₂CH₂CH(CH3)2arrow_forward
- 1. Which among these would be the most stable carbocation?a. Allylicb. Vinylicc. Primaryd. Secondary2. What is the primary reason for the stability of tertiary carbocations?a. Free rotationb. Resonancec. Hyperconjugationarrow_forwardConsider the two alkene additions reactions a. What are the major products for each reaction? b. What is the mechanism for each reaction? c. Which reaction would be faster and why? Use words like “transition-state, intermediate and/or reactant/product stability” in your justification. Draw the reaction coordinate diagram for both to assist in your explanation.arrow_forwardA. REACTIONS OF ALKENES- provide the product(s) or reagents that are needed to accomplish the following transformationsarrow_forward
- 1. 2-bromobutane + cyclohexanol + NaH à (major product) c. 2-butoxycyclohexane a.. 2-butene reaction b. 1-butene d. no e. something else! 2. t-butylbromide + sodium ethoxide in ethanol à (major product) a. 2-methylpropene reaction b. t-butyl ethyl ether c. 1-methylbutene d. no e. something else! 3. potassium t-butoxide + 1-bromobutane in t-butyl alcohol room temperature à (major product) a. 1-butene reaction c. 2-methylpropene d. no b. butyl t-butyl ether e. something else! 4. t-butyl bromide + boiling hot water à (major product) a. 2-methylpropene reaction b. t-butyl ethyl ether c. t-butanol d. no e. something else! 5. 2-chloropropane + acetic acid (2 eq) / KOH (1 eq) / DMF à(major product) c. b. d. no reaction e. something а. HO. else! Br KOH / DMSO 6. b. 2-methyl-1-propanol d. 1,2- a. 2-methylpropene propanediene c. no reaction e. something else! 7. cyclopentanol+ NaH + DMSO + bromopropane à(major product) a. cyclopentene reaction b. propene e. something else!! c. propyl cyclopentyl…arrow_forwardFor Sn1 and Sn2 reactions, explain why one type of carbon should react faster than others.arrow_forwarda. Design a route for the preparation of 1-hexyne from ethyne (acetylene) b. Design a route for the preparation of 3-hexyne from a suitable haloalkane starting materialarrow_forward
- In Chapter 18, we will learn about the hydrolysis of acetals to aldehydes and ketones. Four of the seven steps in the mechanism for this process are shown in the conversion of acetal A to hemiacetal E. a.Add curved arrows for each step. b.Draw another resonance structure for C. c.Identify the nucleophile and electrophile in Step [3]. d.Which steps are Brønsted–Lowry acid–base reactions?arrow_forwarda. What are all the monochlorination product of the reaction with the alkylhalideabove? For each product calculate their relative percentages for the reaction b. What is the Major product formed by the monobromination product of thereaction? Draw the arrow pushing mechanism for the initiation, propagation andtermination steps.arrow_forward5. Which of the following is a true statement? A. Electrophile must be electron deficient. B. Steric effect contributes to the SN1 reactivity of tertiary alkyl halides. C. Retention products could be observed in SN2 reaction. D. The nucleophilicity of a species is equal to its basicity. E. Non-polar solvent is suitable for nucleophilic substitution.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning