(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
Organic Chemistry
- (a) How will you convert the following :(i) Propanone to Propan-2-ol (ii) Ethanal to 2-hydroxy propanoic acid(iii) Toluene to benzoic acid(b) Give simple chemical test to distinguish between :(i) Pentan-2-one and Pentan-3-one (ii) Ethanal and Propanalarrow_forwardDraw line structures of the following compounds and the product you would obtain from the reduction of each.(a) Isopropyl methyl ketone (b) p-Hydroxybenzaldehyde(c) 2-Methylcyclopentanonearrow_forward4. 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_forward
- Reaction of p-nitroaniline with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with N,N-diethylaniline.arrow_forwardArrange the members of each group in order of decreasing basicity: (a) Ammonia, aniline, methylamine (b) Acetanilide, aniline, N-methylaniline (c) 2,4-Dichloroaniline, 2,4-dimethylaniline, 2,4-dinitroaniline (d) 3,4-Dichloroaniline, 4-chloro-2-nitroaniline, 4-chloro-3-nitroaniline (e) Dimethylamine, diphenylamine, N-methylanilinearrow_forwardPredict which member of each pair is more acidic, and explain the reasons for your predictions.(a) cyclopentanol or 3-chlorophenol (b) cyclohexanol or cyclohexanethiol(c) cyclohexanol or cyclohexanecarboxylic acid (d) butan-1-ol or 2,2-dichlorobutan-1-olarrow_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_forwardPredict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.(a) PhMgBr, then H3O+ (b) Tollens reagent (c) semicarbazide and weak acid(d) excess ethanol and acid (e) propane-1,3-diol, H+ (f) zinc amalgam and dilute hydrochloric acidarrow_forwardShow how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.(a) Ph3C¬OH (b) (PhCH2)2CHOH (c) PhCONHCH2CH3(d) Ph2CHOH (e) PhCH2OH (f) PhCOOH(g) PhCH2COOCH(CH3)2 PhCH2 C(CH2CH3)2OH(h) (i) HO¬(CH2) 8¬OHarrow_forward
- How could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylaminearrow_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_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-benzylpyridinarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning