EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 12, Problem 44P
Interpretation Introduction
Interpretation:
The value for the relative east of removing a hydrogen atom from tertiary, secondary and primary hydrogen carbons by a chlorine radical has to be given.
Concept introduction:
Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.
Chlorine radical forms a tertiary radical five times faster than a primary radical and it forms a secondary radical 3.8 times faster than a primary radical.
Relative rates of alkyl radical formation by a chlorine radical at 125 °C.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.
Radical Mono-Chlorination of pentane is a poor way to prepare 1-chloropentane, but radical
chlorination of neopentane, (CH3)4C, is a good way to prepare neopentyl chloride. Write an
equation for both of these reactions and explain why this is.
Pentane
Neopentane
The compound below is treated with chlorine in the presence of
light.
CH3
CH3CHCH,CH3
Draw the structure for the organic radical species produced by
reaction of the compound with a chlorine atom. Assume reaction
occurs at the weakest C-H bond.
• You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
Chapter 12 Solutions
EBK ORGANIC CHEMISTRY
Ch. 12.2 - Prob. 1PCh. 12.2 - Write the steps for formation of...Ch. 12.3 - Prob. 3PCh. 12.4 - How many alkyl chlorides are obtained from...Ch. 12.4 - Prob. 6PCh. 12.5 - Prob. 8PCh. 12.5 - a. Would chlorination or bromination produce a...Ch. 12.5 - Show how the following compounds could be prepared...Ch. 12.6 - Prob. 12PCh. 12.7 - Prob. 13P
Ch. 12.7 - Prob. 14PCh. 12.8 - Prob. 15PCh. 12.8 - Draw the stereoisomers of the major...Ch. 12.9 - Prob. 18PCh. 12.9 - How many allylic substituted bromoalkenes are...Ch. 12.9 - a. How many stereoisomers are formed from the...Ch. 12.9 - Prob. 21PCh. 12.9 - Prob. 22PCh. 12.10 - Prob. 23PCh. 12.11 - How many atoms share the unpaired electrons in...Ch. 12.11 - Prob. 25PCh. 12 - Prob. 26PCh. 12 - Prob. 27PCh. 12 - Prob. 28PCh. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Prob. 33PCh. 12 - Prob. 34PCh. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - Prob. 37PCh. 12 - a. What five-carbon alkene forms the same product...Ch. 12 - Prob. 39PCh. 12 - Starting with cyclohexane, how could the following...Ch. 12 - a. Propose a mechanism for the following reaction:...Ch. 12 - What stereoisomers are obtained from the following...Ch. 12 - Prob. 43PCh. 12 - Prob. 44PCh. 12 - Prob. 45PCh. 12 - Draw the products of the following reactions,...Ch. 12 - Prob. 47PCh. 12 - Prob. 48PCh. 12 - Prob. 49PCh. 12 - Explain why the rate of bromination of methane...Ch. 12 - Prob. 51PCh. 12 - Prob. 1PCh. 12 - Prob. 2PCh. 12 - Prob. 3PCh. 12 - Prob. 4P
Knowledge Booster
Similar questions
- 2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardWhen 2-methylpropane is monochlorinated in the presence of light at room temperature, 36% of the product is 2-chloro-2-methylpropane and 64% is 1-chloro-2-methylpropane. From these data, calculate how much easier it is to remove a hydrogen atom from a tertiary carbon than from a primary carbon under these conditions.arrow_forwardFree‑radical halogenation can occur with chlorine and a source of direct UV radiation or sunlight. Chlorination of 2,4‑dimethylpentane via radical halogenation leads to the formation of all three of the products shown. Estimate the relative percentages of each product that will be formed using this means of halogenation. Presume that 1 equivalent of chlorine is used.arrow_forward
- Free radical halogenation is used to replace one or more hydrogens on an alkane with one or more halogens (either chlorine or bromine). It is a substitution reaction. A student performs a free radical bromination on 3-methyl-pentane (5.88 g) to create the desired product of 3-bromo-3-methyl-pentane. The product mix, which hopefully contains almost all 3-bromo-3-methyl-pentane, is cleaned up by passing it through a gas chromoatograph, which separates out the 3-bromo-3-methyl-pentane from any undesired products made during the reaction (undesired products are created frequently in free radical halogenation). The initial product mix weighed 9.45 g; the purified 3-bromo-3-methyl-pentane weighed 7.21 g. What is the student's percent recovery?arrow_forwardThe chlorination of ethane produces many by-products. One by-product that forms in small amounts is 2-chlorobutane. Suggest a mechanism for the formation of 2-chlorobutane from the radical chlorination of ethane. (NOTES: intermediates can only have one radical, 2-chlorobutane should be the product of your termination step, any intermediate radical formed during the propagation phase can be used in the termination step)arrow_forwardDefine the Mechanism of the Radical Addition of HBr to an Alkene ?arrow_forward
- Photochemical chlorination of 2,2,4-trimethylpentane gives four isomeric monochlorides. (a) Write structural formulas for these four isomers. (b) The two primary chlorides make up 65% of the monochloride fraction. Assuming that all the primary hydrogens in 2,2,4-trimethylpentane are equally reactive, estimate the percentage of each of the two primary chlorides in the product mixture.arrow_forwardWrite the propagation steps leading to the formation of dichloromethane (CH2Cl2) from chloromethanearrow_forwardCompounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is:arrow_forward
- 7. The reaction of methoxide anion with bromoethane to yield the ether ethyl methyl ether and the bromide anon (Br-) is an excellent example of a general reaction type called Sy2 (substitution nucleophilic bimolecular): CH,0+ CH,СH-Br a CH3-0-CH,СH; + Br- a. Change in enthalpy is -103 kJ/mol; the change in entropy is + 0.025 kJ/mol-K. Calculate DG at 300K. b. Is the reaction endergonic or exergonic? c. Is the reaction endothermic or exothermic? d. Use curved arrows to show the complete mechanism. Reaction of 2-methyl-1-butene with H-Cl could yield TWO alkyl chloride products. Draw and name 8. them.arrow_forward196. Subject : - Chemistryarrow_forwardfluorination of alkanes is highly exothermic. Per Hammond’s postulate, assume that the transition state for radical fluorination is almost identical to the starting material. Assuming this fact, estimate the fraction of each monofluoro product formed in the fluorination of 2-methylbutane.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning