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Interpretation:
The effect of increasing solvent polarity on the rate of each of the given nucleophilic substitution reaction is to be determined.
Concept introduction:
Electrophiles are electron-deficient species, which has positive or partially positive charge. Lewis acids are electrophiles, which accept electron pair.
Nucleophiles are electron-rich species, which has negative or partially negative charge. Lewis bases are nucleophiles, which donate electron pair.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
Nucleophilic substitution reaction is a reaction in which an electron-rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
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Chapter 6 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Answer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrowsarrow_forwardDefine the Mechanism of the Radical Addition of HBr to an Alkene ?arrow_forwardFollowing is a balanced equation for bromination of toluene.(a) Using the values for bond dissociation enthalpies given in Appendix 3,calculate ∆H0for this reaction.(b) Propose a pair of chain propagation steps and show that they add up to theobserved reaction.(c) Calculate ∆H0for each chain propagation step.(d) Which propagation step is rate-determininarrow_forward
- Predict the most likely site of attack in electrophilic aromatic substitution. (a) OCH, (b) OH (0) (d) OCH, Br Br (0) NO, (9) NH,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_forwardPredict how the bond, shown in each of the following compounds will break with the aidof the appropriate arrow(s). Also give the structure(s) of the species formed in eachreaction.(a) CH3── I →(b) Q ── Q →arrow_forward
- Only one of the chlorine atoms in the molecule, 3,4-dichloronitrobenzene, will undergo nucleophilic substitution. Indicate which position will react and provide the expected product for the given reaction using reaction intermediates (resonance structures).arrow_forwardDraw a Lewis structure of sodium ethyl mercaptide (NaSC2H5), showing all relevant lone pairs and formal charges. Based on the structure you drew, do you expect that it would act as a good nucleophile? Do you expect it to act as a strong base?arrow_forward6. (Chapter 15-Q37) Indole is an aromatic heterocyclic that has a benzene ring fused to a pyrrole ring. Answer the following questions. Indole 6(a) What is the hybridization of N in this molecule? = 6(b) How many pi electrons N contributes to the ring? = 6() Which orbitals contribute to form a sigma bond between N and H in this molecule? = 6(c) What is the electronic relationship of Indole to naphthalene? Give the answer by comparing number of rings and number of pi electrons in both compounds, write x rings, y pi electrons=|arrow_forward
- (b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2- butene. Write the mechanism for the reaction.arrow_forwardPlease give the main substitution product for each of the following reactions, and indicate the dominant mechanism: (a) 1-bromopropane + NaOCH3 → (b) 3-bromo-3-methylpentane + NaOC2H5 →arrow_forwardAlkyl halides can be reduced to alkanes by a radical reaction with tributyltin hydride, (C4H9)3SnH, in the presence of light (hv). Propose a radical chain mechanism by which the reaction might occur. The initiation step is the light-induced homolytic cleavage of the Sn-H bond to yield a tributyltin radical.arrow_forward
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