Concept explainers
Interpretation:
The reactants of the given reactions are to be deduced.
Concept introduction:
The Grignard reagent or RMgX is a reagent that can be prepared from an alkyl halide and magnesium in the ether. It adds on the alkyl group to the carbonyl moiety and converts the
Wittig reagent or alkyl phosphonium ylide, in presence of base, reacts with carbonyl to form an alkene.
Alcohols can be converted to ethers by the reaction of an alkyl halide with sodium hydride.
Alcohols can be converted to
Alkyl halides react with potassium cyanide to form nitriles.
Carbonyl compound reacts with hydrazine and KOH to form
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EBK ORGANIC CHEMISTRY
- (a) (b) (c) Suggest a synthesis of the following alkene (A) using a Wittig reaction strategy. Draw the starting material(s), key reagent and a full reaction mechanism including an explanation of the observed geometry. Which of the following (B) and (C) will favour the enol form? Briefly explain your reasoning. Predict the product(s) and provide a mechanism for each of the following transformations: (i) (ii) OMe OMe Base OEt NaOEtarrow_forwardShow how you can synthesize the following compounds starting with benzene, toluene, and alcohols containing no morethan four carbon atoms as your organic starting materials. Assume that para is the major product (and separable fromortho) in ortho, para mixtures.(a) pentan-1-amine (b) N-methylbutan-1-aminearrow_forwardWhich reactions will produce the desired product in good yield? You may assume thataluminum chloride is added as a catalyst in each case. For the reactions that will not givea 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-butylbenzenearrow_forward
- Nucleophilic 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) m-cresol (b) p-n-butylphenolarrow_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_forwardAnswer ALL parts of this question. (a) Compound Z is a tertiary aromatic amine with the formula, C8H11N. Provide a chemical structure for compound Z. (b) Provide a reaction scheme for the preparation of nitrous acid. (c) Draw the structure of the product formed exclusively when nitrous acid reacts with Z. (d) Give a curly arrow mechanism for the preparation of the yellow azo-dye from the reaction of Z with benzenediazonium chloride.arrow_forward
- 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_forwardStarting with 2-methylpropene, outline a synthesis of (a) (CH3)3COH (b) (CH3)2C(OH)CH2Brarrow_forwardDraw a structural formula for the alcohol formed by treating each alkene with borane in tetrahydrofuran (THF) followed by hydrogen peroxide in aqueous sodium hydroxide, and specify stereochemistry where appropriate. (a) (d) (b) (e) (c)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 methoxidearrow_forwardGuiding your reasoning by retrosynthetic analysis, show how you could prepare each of the following compounds from the given starting material and any necessary organic or inorganic reagents. All require more than one synthetic step. (a) Cyclopentyl iodide from cyclopentane (b) 1-Bromo-2-methylpropane from 2-bromo-2-methylpropane (c) meso-2,3-Dibromobutane from 2-butyne (d) 1-Heptene from 1-bromopentane (e) cis-2-Hexene from 1,2-dibromopentane (f) Butyl methyl ether (CH3CH2CH2CH2OCH3) from 1-butenearrow_forwardApply 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
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