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ORGANIC COMPOUNDS CONTAINING C, H AND O
Study Material
ORGANIC COMPOUNDS CONTAINING C, H AND O
Very Short Answer Questions
Q1. Explain why propanol has higher boiling point than that of the hydrocarbon -butane.
Q2. Alcohols are comparatively more soluble in water than hydrocarbons of comparable molecular masses. Explain this fact.
Q3. Give the structures and IUPAC names of monohydric phenols of molecular formula. $\ce{ C7H8O}$
Q4. Give the reagents used for the preparation of phenol from chlorobenzene.
Q5. Preparation of ethers by acid dehydration of secondary or tertiary alcohols is not a suitable method. Give reason.
Q6. Write the mechanism of the reaction of $\ce{ Hl}$ with methoxymethane.
Q7. Name the reagents used in the following reactions. i). Oxidation of primary alcohol to carboxylic acid ii). Oxidation of primary alcohol to aldehyde
Q8. Write the equations for the following reactions. i). Bromination of phenol to 2,4,6-tribromophenol ii). Benzyl alcohol to benzoic acid.
Q9. Identify the reactant needed to form t-butylalcohol from acetone.
Q10. Write the structures for the following compounds i). Ethoxyethane ii). Ethoxybutane iii). Phenoxyethane
Q11. Arrange the following compounds in increasing order of their property Indicated- (i). Acetaldehyde, Acetone, Methyl t.butyl ketone reactivity towards $\ce{ HCN}$ ii). Floroacetic acid, monochloroacetic acid, Acetic acid and Dichloroacetic acid (acid strength)
Q12. Write the reaction showing a-halogenation of carboxylic acid and give its name.
Q13. Although phenoxide ion has more number of resonating structures than carboxylate ion carboxylic acid is a stronger acid than phenol. Why?
Q14. How do you distinguish acetophenone and benzophenone?
Q15. Explain the position of electrophilic substitution in benzoic acid.
Q16. Write equations showing the conversion of- i) Acetic acid to Acetyl chloride ii) Benzoic acid to Benzamide
Q17. An organic acid with molecular formula $\ce{ C8H8O2}$ on decarboxylation forms Toluene. Identify the organic acid.
Q18. List the reagents needed to reduce carboxylic acid to alcohol.
Q19. Write the mechanism of esterification.
Q20. Compare the acidic strength of acetic acid, Chloroacetic acid, benzoic acid and Phenol.
Q1. Draw the structures of all isomeric alcohols of molecular formula $\ce{ C5H12O}$ and give their IUPAC names and classify them as primary, secondary and tertiary alcohols.
Q2. While separating a mixture of ortho and para nitrophenols by steam distillation, name the isomer which will be steam volatile. Give reason.
Q3. Give the equations for the preparation of phenol from Cumene.
Q4. Write the mechanism of hydration of ethene to yield ethanol.
Q5. Explain the acidic nature of phenols and compare with that of alcohols.
Q6. Write the products formed by the reduction and oxidation of phenol.
Q7. Ethanol with $\ce{ H2SO4}$, at $\ce{ 443K}$ forms ethane while at $\ce{ 413 K}$ it forms ethoxy ethane. Explain the mechanism.
Q8. Account for the statement: Alcohols boil at highet temperature than hydrocarbons and ethers of comparable molecular masses.
Q9. Explain why in anisole electrophilic substitution takes place at ortho and para positions and not at meta position.
Q10. Write the products of the following reactions:
Q11. Write the equations of any aldehyde with Fehlings reagent.
Q12. What is Tollens reagent? Explain its reaction with Aldehydes.
Q13. Write the oxidation products of: Acetaldehyc, Acetone and Acetophenone
Q14. Explain why Aldehydes and ketones undergoes nucleophilic addition while alkenes undergoes electrophilic addition though both are unsaturated compounds.
Q15. Write the IUPAC names of the following: i) $\ce{ CH2CH2CH(Br) CH2COOH}$ ii) $\ce{ Ph.CH2COCH2 COOH}$ iii) $\ce{ CH3.CH(CH3)CH2COOC2H5}$
Q16. Arrange the following in the increasing order of their acidic strength: Benzoic acid, 4-Methoxybenzoic acid, 4-Nitrobenzoic acid and 4-Methylbenzoic acid.
Q17. Describe the following: i) Cross aldol condensation ii) Decarboxylation
Q18. Explain the role of electron withdrawing and electron releasing groups on the acidity of carboxylic acids.
Q19. Draw the structures of the following derivatives: i) Acetaldehydedimethylacetal ii) The ethylene ketal of hexan-3-one iii) The methyl hemlacetal of formaldehyde.
Q20. An organic compound contains 69.77% carbon, 11.63% hydrogen and rest oxygen. The molecular mass of the compound is 86. It doesnot reduce Tollens' reagent but forms sodium hydrogensulphite adduct and gives +ve lodoform test. On vigorous oxidation forms ethanoic and propanoic acids. Write the possible structure of the compound.
Q1. Write the IUPAC name of the following compounds:
Q2. Write structures of the compounds whose IUPAC names are as follows: i).2. Methyl butan-ol ii) 1-Phenylprpan-2-ol iii) 3,5-Dimethylhexane-1,3,5-triol iv) 2,3-Diethylphenol v) vi) 2-Ethoxy-3-methylpentane 1-Ethoxypropane vii) Cyclohexylmethanol viii) 3-Chloromethylpentan-1-ol
Q3. Write the equations for the preparation of phenol using benzene, conc. $\ce{ H2SO4}$, and $\ce{ NaOH}$.
Q4. Illustrate hydroboration-oxidation reaction with a suitable example.
Q5. Write the IUPAC name of the following compounds: CH OHfi.
Q6. How will you synthesise: i). 1-Phenylethanol from a suitable alkene ii). Cyclohexylmethanol using an alkyl halide by an SN2 reaction. iii). Pentan-1-ol using a suitable alkyl halide.
Q7. Explain why. i). ortho nitrophenol is more acidic than ortho methoxyphenol. ii). OH group attached to benzene ring activates it towards electrophilic substitution.
Q8. With a suitable example write equations for the following: i). Kolbe's reaction ii). Reimer-Tiemann reaction. iii). Williamsons ether synthesis.
Q9. How are the following conversions carried out? i) Benzyl chloride to Benzyl alcohol ii) Ethyl magnesium bromide to Propan-1-ol iii) 2-butanone to 2-butanol
Q10. Write the names of the reagents and equations for the preparation of the following ethers by Williamson's synthesis: i). 1-?????????opane ii). Ethoxybenzene iii). 2-Methoxy-2-methylpropane iv). 1-Methoxyethane
Q11. How is 1-propoxypropane synthesized from propan-1-ol? Write mechanism of this reaction.
Q12. Explain the fact that in aryl alkyl ethers the alkoxy group activates the benzene ring towards electrophilic substitution
Q13. Write equations of the below given reactions: i) Alkylation of anisole ii) Nitration of anisole iii) Friedel-Crafts acetylation of anisole
Q14. Show how you would synthesize the following alcohols from appropriate alkenes? L CH OH OH
Q15. Explain why phenol with bromine water forms 2, 4, 6-tribromophenol while on reaction with bromine in CS, at low temperatures forms para-bromophenol as the major product.
Q16. Explain the following terms. Give an example of the reaction in each case. i). Cyanohydrin ii). Acetal iv). Aldol v). Hemiacetal iii). Semicarbazone vi). Oxime
Q17. Name the following compounds according to IUPAC system of nomenclature: i). $\ce{ CH3CH(CH3)CH2CH2CHO}$ iii). $\ce{ CH3CH=CHCHO}$ ii). $\ce{ CH3CH2COCH(C2H5)CH2CH2CI}$ iv). $\ce{ CH3COCH2COCH3}$
Q18. Draw the structures of the following compounds. i). 3-Methylbutanal ii). p- Nitropropiophenone iii). P-Methylbenzaldehyde iv). 3-Bromo-4-phenylpentanoic acid
Q19. Write the IUPAC names of the following ketones and Aldehydes. Wherever possible, give also common names. i). $\ce{ CH3CO(CH2)4CH3}$ ii). $\ce{ CH3(CH2)5 CHO}$ iii). $\ce{ CH3CH2CHBrCH2CH(CH3)CHO}$ iv). $\ce{ PhCH=CHCHO}$ vi). $\ce{ PhCOPh}$ 65. 66 67
Q20. Draw the structures of the following derivatives. i). The 2,4-dinitrophenylhydrazone of benzaldehyde ii). Cyclopropanone oxime iii). Acetaldehyde hemiacetal iv). The Semicarbazone of cyclobutanone
Q21. Predict the products formed when Cyclohexanecarbaldehyde reacts with following reagents. i). $\ce{ PhMgBr}$ and then $\ce{ H3O^+}$ii). Tollens reagent iii). Semicarbazide and weak acid iv). Zinc amalgam and dilute $\ce{ HCl}$
Q22. Which of the following compounds would undergo aldol condensation? Write the structures of the products expected. i). 2-Methylpentanal ii) 1-Phenylpropanone A1- iii). Phenyl acetaldehyde iv). 2,2-Dimethylbutanal
Q23. An organic compound $\ce{ A (C9H10O)}$ forms $\ce{ 2,4-DNP}$ derivative, reduces Tollens' reagent and undergoes Cannizaro reaction. On vigorous oxidation it gives 1.2- benzenedicarboxylic acid. Identify the compound.
Q24. How do you distinguish the following pairs of compounds? i). Propanal and propanone ii). Acetophenone and benzophenone iii). Phenol and benzoic acid iv). Pentan-2-one and Pentan-3-one
Q25. How are the following conversions carried in not more than two steps? i). Ethanol to 3-hydroxybutanal ii) Bromobenzene to 1-Phenylethanol iii). Benzaldehyde to -Hydroxyphenylacetic acid iv). Benzaldehyde to benzophenone
Q26. Describe the following.i) Acetylation ii). Cannizaro reaction iii) Cross aldol condensationiv iv) Decarboxylation
Q27. Complete each synthesis by giving the missing starting material, reagent or product. CH.CH KMnO KOH, heat L COOH COOH R SOCI heat 111. Iv. (1) 0, (11) Zn-HO
Q28. Explain how methyl ketones are distinguished from other ketones. Write the equations showing it.
Q29. Write the equations showing the conversion of the following along with reagents: i) 1-phenylpropane to Benzoic acid ii) Benzamide to Benzoic acid iii) Ethyl butanoate to Butanoic acid.
Q30. Write the products and reagents needed for the below given conversions: 13-Nitrobromobenzene to 3-Nitrobenzoic acid 1) 4-Methylacetophenone to Benzene-1,4-dicarboxylic acid