Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 4, Problem 4.49SP
(a)
Interpretation Introduction
To determine: The structure of three monochlorinated products of pentane.
Interpretation: The structures of three monochlorinated products of pentane are to be drawn.
Concept introduction: The
(b)
Interpretation Introduction
To determine: The ratio in which primary and secondary monochlorinated products would be formed.
Interpretation: The ratio in which primary and secondary monochlorinated products would be formed is to be predicted.
Concept introduction: The chemical reaction which proceeds through the formation of radicals is known as chain reaction. It involves three steps, initiation, propagation and termination. The initiation step occurs in the presence of light. The quantum yield of chain reactions is very high.
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2-Methyl-2-butene reacts with HBr in the presence of peroxide to give
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c. a tertiary alkyl bromide.
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A certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the
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10. In free-radical substitution reaction of alkanes with halogens under uv light,
A. the photolytic breaking of the halogen is the rate determining step.
B. the abstraction of hydrogen from alkane by the halogen radical is the rate determining step
C. the formation of alkylradical is the rate determining step.
D. the formation of halogen radical is the rate determining step.
11. Which of the following processes could be the termination step in free radical substitution reaction?
A. C₂H6 ---→ 2CH3-
B. C₂H6 +H --⇒ H₂ + C₂H5
C. CH3 + CH3 --→ C₂H6
D. C₂H5 --→ C₂H4 + H
Chapter 4 Solutions
Organic Chemistry (9th Edition)
Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3PCh. 4.3C - Prob. 4.4PCh. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...
Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14PCh. 4.10 - Prob. 4.15PCh. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21PCh. 4.13B - Prob. 4.22PCh. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25PCh. 4.15 - Prob. 4.26PCh. 4.15 - Prob. 4.27PCh. 4.16A - Prob. 4.28PCh. 4.16A - Prob. 4.29PCh. 4.16B - Prob. 4.30PCh. 4.16C - Prob. 4.31PCh. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33PCh. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SPCh. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SPCh. 4 - Prob. 4.42SPCh. 4 - Prob. 4.43SPCh. 4 - Prob. 4.44SPCh. 4 - Prob. 4.45SPCh. 4 - Prob. 4.46SPCh. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SPCh. 4 - Prob. 4.50SPCh. 4 - Prob. 4.51SPCh. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SPCh. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SPCh. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SPCh. 4 - lodination of alkanes using iodine (I2) is usually...
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- 10. In free-radical substitution reaction of alkanes with halogens under uv light, A. the photolytic breaking of the halogen is the rate determining step. B. the abstraction of hydrogen from alkane by the halogen radical is the rate determining step C. the formation of alkylradical is the rate determining step. D. the formation of halogen radical is the rate determining step. 11. Which of the following processes could be the termination step in free radical substitution reaction? A. C₂H6 ---→ 2CH3 B. C₂H6 +H. --→ H₂ + C₂H5 C. CH3 + CH3 --→ C₂H₂ D. C₂H5 --→ C₂H4 + H 12. Which of the following is the most stable carbonium ion intermediate? A. primary carbonium ion B. secondary carbonium ion C. tertiary carbonium ion D. allyl carbonium ionarrow_forwardWhich of the statements given below is false? A. Octanol is soluble in ligroin, while it is insoluble in water.B. By determining the density of hexane and toluene, which are an example of a hydrocarbon, by pictogram, we can obtain information about their physical properties.C. The reaction between an alkene and a halogen is the reaction reaction.D. The reaction of an olefin sample with bromine in carbon tetrachloride is an addition reaction.E. An olefin sample removes the color of Brominated water, while an alkane sample causes the yellow orange color to remain.arrow_forward12.) If the enthalpy of the reaction was at 298 K, what would be the enthalpy of hydrogenation of ethylene to ethane at 373 K? A.) -1.48 kJ/mol B.) +1.48 kJ/mol C.) -138.42 kJ/mol D.) -135.46 kJ/mol E.) +135.46 kJ/molarrow_forward
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- * Explain the chemical foundation:a. The addition of water and alcohol to alkenes is only possible under. Acid catalysis.b. Electrophilic addition reactions are not stereospecific (except in the case of X2 addition).c. Regioselectivity in the X2 addition reactions, even though carbocations are not formed in this mechanism.arrow_forwardFor each reaction identify the reaction type. Reaction Туре a. Methylbenzene and bromine in the presence of ultraviolet light forming 1- bromo-2-methylbenzene and hydrogen bromide. b. 2-methyldecane plus hydrogen reacts to produce heptane and butane c. Hex-2-ene plus hydrogen chloride produces 2-chlorohexane. d. Propane plus pentane reacts to produce 1,2-dimethylcyclohexane and hydrogenarrow_forwardDetermine the product of the reaction considering the conditions given. A. No product will be formed B. 2-methoxy-2,3,3-trimethylpentane C. 2,3,3-trimethyl-1-pentanearrow_forward
- 1. Consider the solubility and boiling point of the following pair of compounds: n-butyl alcohol and diethyl ether. The boiling points for the compounds are 118 °C and 35 °C respectively. The solubility for both compounds is the same (8g/100g water). Explain this observation for (i) boiling point disparity; (ii) solubility similarity a. H-bonds form in diethyl ether; n-butyl alcohol forms H-bonds in water b. H-bonds form in n-butyl alcohol; diethyl ether forms H-bonds in water c. H-bonds in n-butyl alcohol; Both compounds form H-bonds in water d. Both compounds form H-bonds; Both compounds form H-bonds in water 2. Account for the bond angle differences between (i) H-C-H (109.5°) in methane and H-S-H (90°); H-C-H (109.5°) and H-O-H (107.5°) in water. a. The H-S-H has two lone pairs; The H-O-H has two lone pairs b. The H-S-H has no hybridization at p-orbitals; The H-O-H has two lone pairs c. The H-S-H has two lone pairs; The H-O-H has no hybridization…arrow_forwardGiven here are 3 compounds. Compound A: 2,3-dimethylbutane Compound B: 3,4-dimethylhexane Compound C: 4-methylhexane i. List two (2) physical properties and two (2) chemical properties for compounds B. ii. Discuss the sequence of compounds A, B, and C according to their boiling point. iii. Predict the complete chemical reaction for the combustion of compound B iv. Label the carbon and hydrogen classification for compounds A, B, and C.arrow_forward1. Which carbonyl group of the given compound is most reactive for nucleophilic addition reaction? a. All have equal reactivity b. Carbonyl Group 1 c. Carbonyl Group 2 d. Carbonyl Group 2. An aldehyde commonly exhibits a nucleophilic addition type of reaction. When a nucleophile attacks a carbonyl carbon, what happens to the oxygen atom in the structure? Refer to the structure below. ~ a. Oxygen atom becomes more electronegative. b. Oxygen atom obtains a net negative charge. c. Oxygen atom transforms to an alkoxide group. d. Oxygen atom acts as the new electrophile. 3. Assign the trivial name of the structure below. a. Diphenylketone b. Benzyl phenylketone c. Diphenyl aldehyde d. Benzyl phenyl aldehydearrow_forward
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