Concept explainers
Interpretation:
The reactivity toward
Concept introduction:
In
A chemical species that has the tendency to donate an electron pair to an electrophile in order to form a
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.
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.
The reactivity depends on the electronegative atoms and halogen atoms in
Strong electronegative atoms are considered strong nucleophiles, which make the favorable condition for
Want to see the full answer?
Check out a sample textbook solutionChapter 6 Solutions
Organic Chemistry
- Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of ∆H° for the following reactions. (a) CH3¬CH3 + I2 ¡ CH3CH2I + HI(b) CH3CH2Cl + HI ¡ CH3CH2I + HCl(c) (CH3)3C¬OH + HCl ¡ (CH3)3C¬Cl + H2O (d) CH3CH2CH3 + H2 ¡ CH3CH3 + CH4 (e) CH3CH2OH + HBr ¡ CH3CH2¬Br + H2Oarrow_forward• PRACTICE PROBLEM 8.24 A, B, and C are alkynes. Elucidate their structures and that of D using the following reaction roadmap. H2, Pt H,, Pt A (C3H14) (C3H14) IR: 3300 cm (1) O3 (2) HOẠC HO, H2, Pt (C3H12) (C3H16) (1) O3 (2) HOAC hol bian vd beeollot Но. ОН AOHarrow_forward7.20 Write the product you would expect from reaction of each of the following alkyl halides with (i) Na+ ¯SCH3 and (ii) NaOH (yellow-green = Cl): (b) (c) (a)arrow_forward
- (a) H. H. 6.44 Which of the following reactions will yield a racemic mixture of products? HCI HBr (a) (c) H2 H2 (b) (d) Pt Ptarrow_forwardO PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)arrow_forward6.49 Reaction of 3,3-dimethyl-1-butene with hydrogen iodide yields two compounds A and B, each having the molecular formula C6H₁3I, in the ratio A:B = 90:10. Compound A, on being heated with potassium hydroxide in n-propyl alcohol, gives only 3,3-dimethyl-1-butene. Compound B undergoes elimination under these conditions to give 2,3-dimethyl-2-butene as the major prod- uct. Suggest structures for compounds A and B, and write a reasonable mechanism for the for- mation of each.arrow_forward
- As shown below, when compound 6a is heated, (1Z, 3Z)cycloheptadiene is formed. When the related compound 6b is heated, however, (1E, 3Z)-cyclodecadiene is formed. Explain these results, and suggest a reason why opening of the five-membered ring in 6a needs a higher temperature than that of the eight-membered ring in 6b. (7 points) H 270 °C H 6a 6b H 190 °Carrow_forward(1) (ii) (iii) (iv) (v) What is the relationship between the compounds [Cl-Ag-SCN]™ and [SCN-Ag-CIJ? Name the compounds whose molecular formulae are given in Question 1(a) (i). Which of the compounds, [Cl-Ag-SCN] and [SCN-Ag-CI], is the more stable? Explain your answer. Draw the boundary surfaces of all 3d orbitals and label these orbitals according to the conventional nomenclature. Clearly draw and label the Cartesian axes. Draw the crystal field splitting diagram for a linear compound, e.g. [Cl-Ag-SCN] or [SCN-Ag-CI], aligned along the z-axis. You only need to indicate the order of the individual d orbitals as a function of the energy. Explain your answer.arrow_forward2.3 Draw correlation diagrams for conrotatory and disrotatory paths for reactions (a) and (b). Label the HOMOS and LUMOS of the starting materials. Predict the geometry of the product of each reaction. (а) H,C H H CH3 H,C CH, (b) > СНCH, CHCH, H,C °CH3arrow_forward
- A tautometric keto (A) – enol(B) equilibrium may be formulated as follows (A) (B) CH3 – COH ß-----------àCH2 – CHOH Given the following bond energies: C – H = 435kJ mol-1 C – C = 368 C==C = 610 C – O = 357 kJmol-1 C==O = 748 kJmol-1 O – H = 462 kJ mol-1 Calculate the enthalpy change in going from Keto form (A) to the enol form (B)arrow_forward7.26 Calculate the degree of unsaturation in the following formulas, and draw five possible structures for each: (b) CsHgO (a) C10H16 (d) C10H1602 (e) CsH₂NO₂ 7.27 How many hydrogens does each of the following compounds have? (a) CsH₂O₂, has two rings and one double bond (b) C₂H₂N, has two double bonds (c) C₂H₂NO, has one ring and three double bonds 7.29 Name the following alkenes: (a) CH₂ CHCH₂CH3 (d) H₂C H₂C H₂C=CHCHCH CH₂ (d) "X CH3 7.31 Name the following cycloalkenes: (a) CH₂ (b) (e) (b) CH₂ CH₂CH3 (c) C7H10Cl₂ (f) CsH10CINO CH₂CHCH₂CH₂CH CH (e) (e) 3-Butyl-2-heptene (f) trans-2,2,5,5-Tetramethyl-3-hexene CH₂CH₂CH₂ CH₂ 7.30 Draw structures corresponding to the following systematic names: (a) (4E)-2,4-Dimethyl-1,4-hexadiene (b) cls-3,3-Dimethyl-4-propyl-1,5-octadiene (c) 4-Methyl-1,2-pentadiene (d) (3E,5Z)-2,6-Dimethyl-1,3,5,7-octatetraene H₂C (c) (F) CH3 (c) CH₂CH3 H₂C=CCH₂CH3 (1) H₂C=C=CHCH₂ Ocimene 7.32 Ocimene is a triene found in the essential oils of many plants. What is its…arrow_forward• PRACTICE PROBLEM 8.12 Treating a hindered alkene such as 2-methyl-2-butene with BH3:THE leads to the for- mation of a dialkylborane instead of a trialkylborane. When 2 mol of 2-methyl-2-butene is added to 1 mol of BH3, the product formed is bis(3-methyl-2-butyl)borane, nicknamed in reagent "disiamylborane." Write its structure. Bis(3-methyl-2-butyl)borane is a useful certain syntheses that require a sterically hindered borane. (The name “disiamyl" comes from "disecondary-iso-amyl," a completely unsystematic and unacceptable name. The name "amyl" is an old common name for a five-carbon alkyl group.) donbyarrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY