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(a)
Interpretation:
The product formed by the reaction of a given compound with one equivalent lithium dimethylcuprate, followed by protonolysis is to be stated.
Concept introduction:
The lithium dimethylcuprate is also known as Gilman reagent. They are
(b)
Interpretation:
The product formed by the reaction of a given compound with one equivalent lithium dimethylcuprate, followed by protonolysis is to be stated.
Concept introduction:
The lithium dimethylcuprate is also known as Gilman reagent. They are organometallic compounds which are a source of nucleophiles. It contains lithium and copper along with alkyl or aryl group. The formula used to denote Gilman reagent is
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Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
- Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forwardplease help with this question. thank you. The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni: Draw the structures of compound B and C. Provide a plausible mechanism to explain the transformation from compound C into compound D. Identify the reagents you would need to convert compound D into compound F (in just two steps). Also identify the structure of compound E.arrow_forwarddon't know Which of the following, when reacted with HCl, would result in the formation of the same major product at both low and high temperatures? (a) (b)arrow_forward
- The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Describe the chemistry involved in the conversion of (B) to (C). You need not present detailed mechanisms. Rather, state what is accomplished by treating (B) with NaOH and then with HCl followed by heating.arrow_forward17. Outline all steps in a possible laboratory synthesis of each of the following from -butyl alcohol, using any inorganic reagents. Follow the general instructions in the box below. (a) n-butyl bromide (b) n-butyl iodide c) n-butyl hydrogen sulfate (d) sodium n-butoxide (e) butanenitrile, CH3CH₂CH₂CH₂CN (f) n-butyraldehyde, CH3CH₂CH₂CHO (g) n-butyric acid, CH3CH₂CH₂COOH (h) n-butane (i) n-butane-1-d, CH3CH₂CH₂CH₂D (j) n-octanearrow_forwardEach of the following reactions has been carried out under conditions such that disubstitution or trisubstitution occurred. Identify the principal organic product in each case. (a) Nitration of p-chlorobenzoic acid (dinitration) (b) Bromination of aniline (tribromination) (c) Bromination of o-aminoacetophenone (dibromination) (d) Bromination of p-nitrophenol (dibromination) (e) Reaction of biphenyl with tert-butyl chloride and iron(III) chloride (dialkylation) (f) Sulfonation of phenol (disulfonation)arrow_forward
- Show 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_forwardEach of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case. (a) o-Cyanoaniline (c) p-Aminoacetophenonearrow_forward18.18 Provide a structural formula for the product from each of the following reactions. (a) (c) (e (1) LDA (2) CH,CH,I NaH CI (b) (d) O. (f Br, CH,CO,H Br, (excess), NaOHarrow_forward
- Deduce the structure of compound C.arrow_forwardGive the structure of the product formed on reaction of ethyl acetoacetate with each of the following: (a) 1-Bromopentane and sodium ethoxide (b) Saponification (basic hydrolysis) and decarboxylation of the product in part (a) (c) Methyl iodide and the product in part (a) treated with sodium ethoxide (d) Saponification and decarboxylation of the product in part (c) (e) 1-Bromo-3-chloropropane and one equivalent of sodium ethoxide (f) Product in part (e) treated with a second equivalent of sodium ethoxide (g) Saponification and decarboxylation of the product in part (f) (h) Phenyl vinyl ketone and sodium ethoxide (i) Saponification and decarboxylation of the product in part (h)arrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward
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