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Concept explainers
Interpretation:
The starting material, which gives the desired product through the given defined reaction on working backward, is to be deduced.
Concept introduction:
Acid catalyzed dehydration is a reaction in which the alcohol is converted into
Elimination reaction: A reaction in which two substituent groups present on adjacent positions are detached and a double bond is formed.
Nucleophilic substitution reaction: A reaction, in which one of the hydrogens of a hydrocarbon, or a
A nucleophile is a molecule or atom with negative charge or a lone pair of electrons.
The reaction in which the halide group is removed through elimination reaction to form the alkene is called dehydrohalogenation.
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Chapter 8 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
- Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures. (a) 3-nitro-4-bromobenzoic acid (b) 3-nitro-5-bromobenzoic acid (c) 4-butylphenol (d) 2-(4-methylphenyl)butan-2-olarrow_forwardWrite equations showing how to prepare each of the following from benzene or toluene and any necessary organic or inorganic reagents. If an ortho, para mixture is formed in any step of your synthesis, assume that you can separate the two isomers. (a) Isopropylbenzene (b) p-Isopropylbenzenesulfonic acid (c) 2-Bromo-2-phenylpropane (d) 4-tert-Butyl-2-nitrotoluene (e) m-Chloroacetophenone (f) p-Chloroacetophenone (g) 3-Bromo-4-methylacetophenone (h) 2-Bromo-4-ethyltoluene (i) 3-Bromo-5-nitrobenzoic acid (j) 2-Bromo-4-nitrobenzoic acid (k) 1-Phenyloctane (l) 1-Phenyl-1-octene (m) 1-Phenyl-1-octyne (n) 1,4-Di-tert-butyl-1,4-cyclohexadienearrow_forwardNucleophilic aromatic substitution provides one of the common methods for making phenols. Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenolarrow_forward
- Apply retrosynthetic analysis to guide the preparation of each of the following compounds from the indicated starting material, then write out the synthesis showing the necessary reagents. (a) 1-Propanol from 2-propanol (b) 1,2-Dibromopropane from 2-bromopropane (c) 1-Bromo-2-propanol from 2-propanol (d) 1-Bromo-2-methyl-2-propanol from tert-butyl bromide (e) 1,2-Epoxypropane from 2-propanol (f) tert-Butyl alcohol from isobutyl alcohol (g) tert-Butyl iodide from isobutyl iodide (h) trans-2-Chlorocyclohexanol from cyclohexyl chloridearrow_forward(a) CH3CHDOH (b) Show how to make these deuterium-labeled compounds, using CD3MgBr and D2O as your sources of deuterium, and any non-deuterated starting materials you wish. (a) CH3CH(OD)CD3 (d) Ph(CD3)2COD (b) CH3C(OH)(CD3)2 (c) CD3CH2CH2OHarrow_forwardPredict the major product or the necessary reagent or reactant to complete each of the following reactions. In the box before each reaction, indicate the mechanism followed by the reaction. (Free radical (FR), SN2, SN1). (b) (a) Clâ‚‚ CHâ‚‚CHâ‚‚OH (a) 1 hv 2 (b) H Br Hâ‚‚O Na+ SCH3 (c) (d) CI "CH3arrow_forward
- Starting with 2-methylpropene, outline a synthesis of          (a)   (CH3)3COH           (b)    (CH3)2C(OH)CH2Brarrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane           (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardWhich reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.  Reagents                                 Desired Product(a) benzene + n-butyl bromide               n-butylbenzene(b) ethylbenzene + tert-butyl chloride         p-ethyl-tert-butylbenzene(c) bromobenzene + ethyl chloride            p-bromoethylbenzene(d) benzamide (PhCONH2) + CH3CH2Cl        p-ethylbenzamide(e) toluene + HNO3, H2SO4, heat            2,4,6-trinitrotoluene (TNT)arrow_forward
- Ethoxide is used as the base in the condensation of ethyl acetate to avoid some unwantedside reactions. Show what side reactions would occur if the following bases were used.(a) sodium methoxide (b) sodium hydroxidearrow_forward2B Suggest a short synthetic route for the preparation of compound D from compound C OH Br COOH C D Note: Apart from compound C, you can also use organic reagents with up to 1 C atom. The number of arrows in the figure above does not necessarily correspond to the number of steps.arrow_forward(c) Answer each of the questions below that relate to acetophenone: Xo (i) (ii) (iii) Draw the structure of the enol form of acetophenone. Give a stepwise mechanism for the conversion of acetophenone into its enol form. Show how each of the three compounds A, B and C below can be prepared from acetophenone. Explain clearly what reactants/reagents would be required in each case. odocor A B Br Carrow_forward
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