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
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EBK ORGANIC CHEMISTRY
- 7.20 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_forward7.51 You have available 2,2-dimethylcyclopentanol (A) and 2-bromo-1,1-dimethylcyclopentane (B) and wish to prepare 3,3-dimethylcyclopentene (C). Which would you choose as the more suitable reactant, A or B, and with what would you treat it? H3C CH3 H3C CH3 H3C CH3 ОН Br A B Carrow_forward7.44 Give the structures of two different alkyl bromides both of which yield the indicated alkene as the exclusive product of E2 elimination. (а) СH;CH—CH, (b) (CH3)2С—СH2 (c) BRCH=CB12 CH3 (d) CH3arrow_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
- Problems 8.29 Give the mechanistic symbols (SN1, SN2, E1, E2) that are most consistent with each of the following statements: (a) Methyl halides react with sodium ethoxide in ethanol only by this mechanism. (b) Unhindered primary halides react with sodium ethoxide in ethanol mainly by this mechanism. (c) When cyclohexyl bromide is treated with sodium ethoxide in ethanol, the major prod- uct is formed by this mechanism. (d) The substitution product obtained by solvolysis of tert-butyl bromide in ethanol arises by this mechanism. (e) In ethanol that contains sodium ethoxide, tert-butyl bromide reacts mainly by this mechanism. (f) These reaction mechanisms represent concerted processes. (g) Reactions proceeding by these mechanisms are stereospecific. (h) These reaction mechanisms involve carbocation intermediates. (i) These reaction mechanisms are the ones most likely to have been involved when the products are found to have a different carbon skeleton from the substrate. (j) Alkyl…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(a) Rank A, B, and C in order of increasing SN2 reactivity. (b) Rank A, B, and C in order of increasing SN1 reactivity.arrow_forward
- • PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forwardPRACTICE PROBLEM 8.20 Specify the alkene and reagents needed to synthesize each of the following diols. OH HO- (a) (b) (c) HO. н он HO (racemic) (racemic)arrow_forward7.66 Diphenhydramine, the antihistamine in Benadryl, can be prepared by the following two-step sequence. What is the structure of diphenhydramine? (1) NaH diphenhydramine Br (2]arrow_forward
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