(a)
Interpretation: The mechanism and the major product formed in the reaction of a secondary
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in
(b)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(c)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is ammonia.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(d)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is HSe-.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(e)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is fluoride ion.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(f)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(g)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is PH3.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(h)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is NH2OH.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
(i)
Interpretation: The mechanism and the major product formed in the reaction of a secondary haloalkane in the polar aprotic solvent needs to be determined if the nucleophile is NCS-.
Concept Introduction: Nucleophillic substitution and elimination reactions are two types of the reactions, playing important role in organic chemistry. In the nucleophillic substitution reaction, a leaving group is replaced with a nucleophile and in the elimination reaction rearrangement takes place resulting formation of an alkene.
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Chapter 7 Solutions
Organic Chemistry: Structure and Function
- 5) Provide the expected mechanism for the following reaction. Please show all intermediates and use arrows to show the movement of electrons (you do not have to show transition states). (1 pt) ii CI NaOH (2 equiv)arrow_forward1) Nucleophilic substitution reaction of alkyl halide is a process when nucleophile replace the leaving group of alkyl halide. Propose the mechanism and product(s) for the following substitution reaction. а) H3C-C- Br OH- +arrow_forwardIn the substitution reaction of 2-chloro-2,4- dimethylpentane with water, the rate at which the alcohol product is formed depends on the concentration of the nucleophile. Select one: True Falsearrow_forward
- Draw the structure of the product/s in each of the following reactions. CuBr NaNO2, HCI, H,O, 0°C (F) (G) Para-methyl- aniline KI CUCN OH- (H) (), (J) phenolarrow_forwardWhen pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results? 1-ethoxypentane 1-methoxypentane 3-ethoxypentane 2-ethoxypentane 2-methoxypentanearrow_forward4) Predict the major product(s) for the following reactions. (8 pts) (a) 1) NaOH, 12 2) H3O (b) EtO (excess) 1) NaOEt, EtOH OEt 2) 3) H3O, heat (c) 1) LDA, THF 2) Br OH (d) Br₂ PBr3 Brarrow_forward
- The reoction below is an exomple of what type of organic reaction? (CHa)NH + CH3-C CH3-C HC CI N(CHJ2 Nucleophilic Addition Nucleophilic Substitution Electrophilic Substitution Tiectrophilic Adstion timintion whnof the folowing omines hos the lowest pa Electrophilic Addition O Elimination Which of the following amines has the lowest pkb? O Trimethylamine O Methylamine O Dimethylamine O Chiloromethylamine Refer to the following reaction mechanism: Reter to the following reaction mechanism red wwouc of slow fast OCH OH OH C-OH CH,0 fast CH,C-O CH,OH AMuming that the finol product in more shoble tmen the reoctant which energy diogrom coneent with the peoposed mechanamarrow_forwardIdentify the structure of the product formed in the following reaction: NHỊNH, KOH OH OH Product? 5 Сarrow_forwardWhich of the following species is the least nucleophilic? HO (CH3)3CO H₂O (CH3)3N CNarrow_forward
- H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3arrow_forwardThe Gabriel synthesis is a two-step preparation for primary amines, with the alkylation of potassium phthalimide constituting the first step as shown here: DMF, heat K-N CI potassium phthalimide A What is the theoretical yield of compound B, in grams, when 313 g of compound A are allowed to react with 187 g of potassium phthalimide? [Hint: cmpd A = 224.07 g/mol; cmpd B = 335.13 g/mol, and potassium phthalimide = 184.99 g/mol]arrow_forward2) How might you prepare 2-phenylethanol from benzyl bromide? More than one step is needed. O 236 Sajjad Oday, 10:36 PMarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning