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(a)
Interpretation:
The isomers:
Concept introduction:
The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.
(b)
Interpretation:
The isomers:
Concept introduction:
The number of NMR signal in a compound is equal to the number of chemically non-equivalent protons present in that compound. The more the shielded proton less will be its chemical shift value and the corresponding signal will be produced at the right-hand side or lower frequency region or vice versa.
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Chapter 16 Solutions
EBK ORGANIC CHEMISTRY
- Describe the characteristic infrared absorption frequencies that would allow you to distinguish between the following pairs of compounds. (a)oct-1-yne and octanenitrile (b) butanoic acid and 3-hydroxybutanalarrow_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_forwardGive a chemical test to distinguish between the following pair of compounds.(i) n-Propylalcohol and isopropylalcohol(ii) Methanol and ethanol(iii) Cyclohexanol and phenol.(iv) Propan-2-ol and 2-methylpropan-2-ol.(v) Phenol and anisole(vi) Ethanol and diethyletherarrow_forward
- (b) Compound C has the molecular formula of C-H12. The IR spectrum shows the important absorption bands at 2950, 2830 and 2250 cm-1 while the 'H NMR spectrum shows two singlets at dH 1.24 (9H) and ôH 1.80 (3H). Based on these spectral data, deduce the structure of compound C.arrow_forwardDescribe the characteristic infrared absorption frequencies that would allow you to distinguish between the following pairs of compounds. (a) cyclohex-2-enone and cyclohex-3-enone (b) cyclohexanol and cyclohexanonearrow_forwardDescribe the characteristic infrared absorption frequencies that would allow you to distinguish between the following pairs of compounds. (a) pentanal and pentan-2-one (b) butanamide and pentan-3-onearrow_forward
- (c) A series of dialkyl ethers react with excess hydrogen bromide, with the following results. Analyze the ether in each case and write out the complete chemical equations. (1) Ether gives a mixture of bromocyclopentane and 1-bromoethane. (ii) Another ether gives one mole of 1,5-dibromopentane per mole of ether.arrow_forward(a) The IR spectrum below shows the important absorption bands for compound A (C7H1402). Its 'H NMR spectrum shows only singlets at &H 1.3, 2.3, 3.9 and 8.5 with the integration ratio of 9:2:2:1. Using all the spectral data, deduce the structure of compound A. 100 50- 2898 2986 1718 3446 1150 0- 4000 3000 2000 1500 1000 500 wavenumber 5. Transmittancearrow_forward(a) Give chemical tests to distinguish between the following pairs of compounds :(i) Pentan-2-ol and Pentan-3-ol (ii) Methanol and Phenol(b) o-nitro phenol is more acidic than o-methoxy phenol. Explain why.arrow_forward
- (a) Give chemical tests to distinguish between :(i) Propanol and propanone (ii) Benzaldehyde and acetophenone(b) Arrange the following compounds in an increasing order of their property as indicated :(i) Acetaldehyde, Acetone, Methyl tert-butyl ketone (reactivity towards HCN)(ii) Benzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(iii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH, (CH3)2CHCOOH (acid strength)arrow_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_forwardWrite structural formulas for the cyclohexadienyl cations formed from aniline (C6H5NH2) during(a) Ortho bromination (four resonance structures)(b) Meta bromination (three resonance structures)(c) Para bromination (four resonance structures)arrow_forward
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