(a)
Interpretation:
4-phenyl-2-butanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(b)
Interpretation:
2-methylhexanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(c)
Interpretation:
3-ethyl-2-pentanone has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(d)
Interpretation:
2-propyl-1,3-propanediol has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(e)
Interpretation:
4-oxopentanoic acid has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(f)
Interpretation:
3-benzyl-5-hexen-2-one has to be synthesized either by acetoacetic ester synthesis or malonic ester synthesis.
(g)
Interpretation:
Cyclopropane
(h)
Interpretation:
Cyclobutylmethyl
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Chapter 19 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- 4. Which of the following compounds can be prepared by a malonic ester synthesis? Show the alkyl halide you would use in each case. (a) Ethyl pentanoate © Ethyl 2-methylbutanoate (b) Ethyl 3-methylbutanoate (d) Ethyl 2,2-dimethylpropanoatearrow_forwardReaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardDraw the structures of the following.arrow_forward
- 1. Predict the products or the reaction of (i) phenylacetaldehyde and (ii) acetophenone with the following reagents: (a) NABH4, then H0+ (c) NH2OH, HCI catalyst (e) 2 CH3OH, HCl catalyst (g) (CH3)3P=CH, (b) Tollens' reagent (cl) CHĄMgBr, then H30+ (t) H2NNH2. KOH (h) HCN, KCNarrow_forwardProvide reagentsarrow_forwardDraw the structure of each compound.(a) o-nitroanisole (b) 2,4-dimethoxyphenol (c) p-aminobenzoic acid(d) 4-nitroaniline (e) m-chlorotoluene (f) p-divinylbenzene(g) p-bromostyrene (h) 3,5-dimethoxybenzaldehyde (i) tropylium chloride(j) sodium cyclopentadienide (k) 2-phenylpropan-1-ol (l) benzyl methyl ether(m) p-toluenesulfonic acid (n) o-xylene (o) 3-benzylpyridinearrow_forward
- Use a Grignard reaction to prepare the following alcohols. (a) 2-Methyl-2-propanol (b) 1-Methylcyclohexanol (c) 3-Methyl-3-pentanol (d) 2-Phenyl-2-butanol (e) Benzyl alcohol (f) 4-Methyl-1-pentanolarrow_forward11. Which compound is the strongest base? (A) m-nitroaniline (B) aniline (C) 4-methylaniline (D) 3-bromo-5-nitroaniline (E) 2,4-dimethylaniline 13 Which of the following compounds has the 12. Which compound is the strongest acid? (A) benzoic acid (B) 4-amino-2-methylbenzoic acid (C) p-nitrobenzoic acid (D) 2,4-dinitroabenzamide (E) 3,5-dinitrobenzoic acid 14 How many H atoms are in the compound: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
- How could you convert each of the following compounds into butanoic acid? Write each step showing all reagents. (a) 1-Butanol (b) 1-Bromobutane (c) 1-Butenearrow_forwardWrite a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) + ethyl bromide (c) Product of part (a) + butyl p-toluenesulfonate (d) Product of part (a) + acetic anhydride (e) o-Cresol + benzoyl chloride (f) m-Cresol + ethylene oxide (g) 2,6-Dichlorophenol + bromine (h) p-Cresol + excess aqueous bromine (i) Isopropyl phenyl ether + excess hydrogen bromide + heatarrow_forwardFollowing is a synthesis for toremifene, a nonsteroidal estrogen antagonist whose structure is closely related to that of tamoxifen. (a) This synthesis makes use of two blocking groups, the benzyl (Bn) group and the tetrahydropyranyl (THP) group. Draw a structural formula of each group and describe the experimental conditions under which it is attached and removed. (b) Discuss the chemical logic behind the use of each blocking group in this synthesis. (c) Propose a mechanism for the conversion of D to E. (d) Propose a mechanism for the conversion of F to toremifene. (e) Is toremifene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning