Chapter 28

The end product (b) in the following sequence of reactions \(\mathrm{CH}_{3} \mathrm{Cl} \stackrel{\mathrm{KCN}}{\longrightarrow}\) (a) \(\stackrel{\mathrm{H}^{\prime} / \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}\) (b) is (a) \(\mathrm{HCOOH}\) (b) \(\mathrm{CH}_{3} \mathrm{NH}_{2}\) (c) \(\mathrm{CH}_{3} \mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\)

\(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O} \frac{\text { diethyl ether }}{\text { Anhyd. } \mathrm{AlCl}_{3}} \rightarrow \mathrm{A}\). Product \(\mathrm{A}\) is (a) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (b) \(\mathrm{CH}_{3} \mathrm{COOCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{5}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}^{2}\)

Which is not true about acetophenone? (1) Reacts with \(\mathrm{I}_{2} / \mathrm{NaOH}\) to form iodoform (2) Reacts with Tollen's reagent to form silver mirror (3) On oxidation with alkaline \(\mathrm{KMnO}_{4}\) followed by hydrolysis gives benzoic acid (4) Reacts to form 2,4 -dinitrophenyl-hydrazone (a) 2 and 4 (b) 2 only (c) \(\mathrm{l}\) and 4 (d) 4 only

Hydrolysis of an ester gives a carboxylic acid which on Kolbe's electrolysis yields ethane. The ester is (a) Methyl methanoate (b) Methyl propanoate (c) Ethyl methanoate (d) Methyl ethanoate

To convert 2 -butanone into propionic acid (a) \(\mathrm{NaOH}+\mathrm{Nal} / \mathrm{H}^{+}\) (b) Fehling's test (c) \(\mathrm{I}_{2} / \mathrm{NaOH} / \mathrm{H}^{+}\) (d) Tollen's reagent

The end product (c) in this reaction, \(\mathrm{CH}_{3} \mathrm{COOH} \stackrel{\mathrm{CaCO}_{3}}{\longrightarrow} \mathrm{A} \stackrel{\text { Heat }}{\longrightarrow \mathrm{B}}\) \(\stackrel{\mathrm{NH}_{2} \mathrm{OH}}{\longrightarrow} \mathrm{C}\), is (a) Acetaldehyde oxime (b) Aceto oxime (c) Acetamide (d) Ethane nitrile

In the following sequence of reactions: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} \stackrel{\mathrm{KMnO}_{4}}{\longrightarrow}\) (a) \(\stackrel{\mathrm{SOCl}_{2}, \mathrm{NH}_{3}}{\longrightarrow}\) (b) \(\mathrm{Br}_{2}+\mathrm{NaOH}\) (c) the end product (c) is (a) Acetone (b) Ethylamine (c) Acetic acid (d) Methyl amine

Which of the following will give yellow precipitate with \(\mathrm{I}_{2} / \mathrm{NaOH}\) ? 1\. \(\mathrm{ICH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) 2. \(\mathrm{CH}_{3} \mathrm{COOCOCH}_{3}\) 3\. \(\mathrm{CH}_{3} \mathrm{CONH}_{2}\) 4\. \(\mathrm{CH}_{3} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (a) 1,3 (b) 3,4 (c) 1,2 (d) 1,4

Consider the following substances: 1\. HCHO 2\. \(\mathrm{CH}_{3} \mathrm{CHO}\) 3\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{3}\) 4\. \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) Correct order of reactivity towards nucleophillic addition reaction is: (a) \(1>4>2>3\) (b) \(1>2>4>3\) (c) \(1>3>2>4\) (d) \(1>2>3>4\)

Under Wolff-Kishner reduction conditions, the conversions which may be brought about are 1\. Benzophenone into diphenylmethane 2\. Benzaldehyde into benzyl alcohol 3\. Cyclohexanone into cyclohexane 4\. Cyclohexanone into cyclohexanol (a) 1,2 (b) 1,3 (c) \(1,3,4\) (d) \(2,3,4\)

Place the following acid chlorides in the decreasing order of reactivity to hydrolysis. (1) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl}\) (2) \(\mathrm{p}-\mathrm{O}_{2} \mathrm{NC}_{6} \mathrm{H}_{4} \mathrm{COCl}\) (3) \(\mathrm{p}-\mathrm{CH}_{3} \mathrm{OC}_{6} \mathrm{H}_{4} \mathrm{COCl}\) (a) \(2>1>3\) (b) \(3>1>2\) (c) \(1>2>3\) (d) \(1>3>2\)

Consider the following substances: (1) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCH}_{2} \mathrm{COCH}_{3}\) (2) \(\left(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OCO}\right)_{2} \mathrm{CH}_{2}\) (3) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COOC}_{2} \mathrm{H}_{3}\) (4) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COCH}_{3}\) Place these dicarbonyl compounds in decreasing order of their enol content. (a) \(4>3>2>1\) (b) \(1>4>3>2\) (c) \(1>2>3>4\) (d) \(1>4>2>3\)

Consider the following acids: (1) \(\mathrm{HCN}\) (2) \(\mathrm{HCOOH}\) (3) \(\mathrm{CH}_{3} \mathrm{COOH}\) (4) \(\mathrm{Cl}-\mathrm{CH}_{2}-\mathrm{COOH}\) The acid strengths of these acids are such that (a) \(4>3>1>2\) (b) \(1>3>2>4\) (c) \(2>3>4>1\) (d) \(4>2>3>1\)

Consider the following acids: (1) \(\mathrm{CH}_{3} \mathrm{COOH}\) (2) \(\mathrm{Cl}_{2} \mathrm{CHCOOH}\) (3) \(\mathrm{ClCH}_{2} \mathrm{COOH}\) (3) \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) The correct sequence of acidity is: (a) \(3>1>2>4\) (b) \(2>3>4>1\) (c) \(1>3>4>2\) (d) \(2>4>3>1\)

Consider the following acids: (1) \(\mathrm{o}-\mathrm{HOC}_{6} \mathrm{H}_{4} \mathrm{COOH}\) (2) \(\mathrm{o}-\mathrm{CH}_{3} \mathrm{OC}_{6} \mathrm{H}_{4} \mathrm{COOH}\) (3) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) Arrange these acids in the decreasing order of their acidities. (a) \(\mid>3>2\) (b) \(3>2>1\) (c) \(1>2>3\) (d) \(2>3>1\)

Consider the following statements; Acetophenone can be prepared by I. oxidation of 1 -phenylethanol II. reaction of benzaldehyde with methyl magnesium bromide III. Friedal Crafts reaction of benzene with acetyl chloride IV. Distillation of calcium benzoate Which of the above statements are correct? (a) I and III (b) III and IV (c) II and III (d) I and IV

Compound 'A' (molecular formula \(\mathrm{C}_{3} \mathrm{H}_{\mathrm{s}} \mathrm{O}\) ) is treated with acidified potassium dichromate to form a product 'B' (molecular formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}\) ). 'B' forms a shining silver mirror on warming with ammonical silver nitrate. 'B' when treated with an aqueous solution of \(\mathrm{H}_{2} \mathrm{NCONHNH}_{2}, \mathrm{HCl}\) and sodium acetate gives a product ' \(C^{\prime}\). Identify the structure of ' \(\mathrm{C}^{\prime}\)

Which of the following undergoes aldol condensation? 1\. Acetaldehyde 2\. Propionaldehyde 3\. Benzaldehyde 4\. Trideuteroacetaldehyde. (a) 1,2 (b) \(1,2,3\) (c) \(1,2,4\) (d) 2,4

Which of the following statement(s) is/are correct? (a) The nucleophilic addition of \(\mathrm{HCN}\) to \(\mathrm{CH}_{3}-\mathrm{CH}=\) \(\mathrm{CH}-\mathrm{CHO}\) results in major addition to \(\mathrm{C}=\mathrm{O}\). (b) The nucleophilic addition of \(\mathrm{HCN}\) to \(\mathrm{CH}_{3}-\mathrm{CH}=\) \(\mathrm{CH}-\mathrm{CHO}\) results in major addition to \(\mathrm{C}=\mathrm{C} .\) (c) The nucleophilic addition of \(\mathrm{PhMgBr}\) to \(\mathrm{PhCH}=\) \(\mathrm{CH}-\mathrm{COCMe}_{3}\) results in addition to \(\mathrm{C}=\mathrm{C}\). (d) The nucleophilic addition of \(\mathrm{PhMgBr}\) to \(\mathrm{PhCH}\) \(\mathrm{CH}-\mathrm{CHO}\) results in addition to \(\mathrm{C}=\mathrm{O}\).

On warming with \(\mathrm{I}_{2}\) and aqueous \(\mathrm{NaOH}\), iodoform and sodium succinate are formed. The formula of the compound should be (a) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{COC}_{6} \mathrm{H}_{s}\) (c) \(\mathrm{CH}_{3}^{3}-\mathrm{CO}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{COCH}_{3}\)

\(\mathrm{Ph}-\mathrm{CHO}+\mathrm{NH}_{2} \mathrm{OH} \rightarrow(\mathrm{A})\) Which of the following is/are true about compound (A)? (a) The syn- \((\mathrm{A})\) on treatment with \(\mathrm{PCl}_{5}\) in ether gives N- phenyl formamide. (b) The product (A) exists in 2 isomeric forms. (c) The suitable \(\mathrm{pH}\) for the reaction is between 4 to 6 (d) The anti- (A) on treatment with \(\mathrm{PCl}_{5}\) in ether followed by hydrolysis gives aniline and formic acid.

Which of the following reactions, yield a product with a three membered ring? (a) \(\mathrm{CH}_{3}-\mathrm{C}(\mathrm{O})-\mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Cl} \stackrel{\mathrm{KOH}, \mathrm{H}_{2} \mathrm{O}}{\longrightarrow}\) (b) \(\mathrm{PhCHO}+\mathrm{Br}-\mathrm{CH}_{2}-\mathrm{C}(\mathrm{O})-\mathrm{OEt}\) \(\mathrm{t}-\mathrm{BuO}^{-} / \mathrm{t}-\mathrm{BuOH}\) (c) \(\mathrm{Ph}-\mathrm{CH}=\mathrm{CH}-\mathrm{CH}_{3} \stackrel{\mathrm{mCPBA}}{\longrightarrow}\) (d) 3- bromobutan -2-ol \(-\mathrm{OH} / \mathrm{H}_{2} \mathrm{O}\)

Identify the products formed \((\mathrm{X})\) and (Y) in the following reaction \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}+\mathrm{HCHO}_{\text {conc. } \mathrm{OH}}{\longrightarrow}(\mathrm{X})+(\mathrm{Y})\) (a) \((\mathrm{X})\) is \(\mathrm{HCOO}^{\mathrm{e}}\) (b) \((\mathrm{Y})\) is \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{OH}\) (c) (Y) is \(\mathrm{CH}_{3} \mathrm{OH}\) (d) \((\mathrm{X})\) is \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COO}^{\Theta}\)

A hydrocarbon \(\mathrm{C}_{7} \mathrm{H}_{12}\) on ozonolysis gives a compound which undergoes aldol condensation, giving 1- acetylcyclopentene. The hydrocarbon is

Match the following: List I 1\. \(\mathrm{RCHO}+2 \mathrm{R}^{\prime} \mathrm{OH} \quad\) dry \(\mathrm{HCl}\) gas 2\. \(\mathrm{R}_{2} \mathrm{C}=\mathrm{O}+\mathrm{R}^{\prime} \mathrm{NH}_{2}\) 3\. \(\mathrm{RCH}=\mathrm{O}\) (or \(\mathrm{R}_{2} \mathrm{C}=\mathrm{O}\) ) \(+\) Phenyl hydrazine \(\mathrm{H}^{+}\) 4\. \(\mathrm{PhCHO}+\mathrm{NH}_{2} \mathrm{OH}\) \(\mathrm{H}^{+}\) List II (i) Benzaldehyde oxime (ii) A phenyl hydrazone (iii) A Schiff's base (iv) An acetal The correct matching is: 1 \(\begin{array}{lll}2 & 3 & 4\end{array}\) (a) (iv) (iii) (ii) (i) (b) (iv) (iii) (i) (ii) (c) (iii) (iv) (ii) (i) (d) (i) (ii) (iii) (iv)

Match the following: List I (Compounds to be reduced) 1\. \(\mathrm{BrCH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) 2\. \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COCH}_{3}\) 3\. \(\mathrm{PhCH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{3}\) 4\. \(\mathrm{PhCOCH}_{3}\) List II (most suitable reduction) (i) Clemmensen reduction (ii) Wolf-Kishner reduction (iii) Both The correct matching is: \(\begin{array}{llll}1 & 2 & 3 & 4\end{array}\) (a) (iii) (ii) (ii) (i) (b) (i) (ii) (ii) (iii) (c) (i) (iii) (iii) (ii) (d) (ii) (iii) (ii) (i)

Match the following: List I 1\. Formalin 2\. Trioxane 3\. Ketene 4\. Metaldehyde List II (i) Trimer of \(\mathrm{HCHO}\) (ii) Compounds of the general formula, \(\mathrm{R}_{2} \mathrm{C}=\mathrm{C}=\mathrm{O}\) (iii) A tetramer of acetaldehyde (iv) \(40 \%\) aqueous solution of \(\mathrm{HCHO}\)

Match the following: List I (Reaction) 1\. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}+\mathrm{NaOH} \longrightarrow \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COOH}\) 4\. \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{NaOH}+\mathrm{CO}_{2} \stackrel{\text { 1. heat, 2. } \mathrm{H}^{+}}{\longrightarrow}\) List II (Name of reactions) (i) Rosenmund reduction (ii) Kolbe's reaction (iii) Claisen reaction (iv) Cannizzaro reaction (v) Friedal-Craft's reaction The correct matching is:

Match the following Column-I (a) Cannizzaro reaction (b) Aldol condensation (c) Benzoin condensation (d) Claisen condensation Column-II (p) \(\mathrm{PhCHO}\) (q) \(\mathrm{CH}_{3} \mathrm{CHO}\) (r) \(\mathrm{O}\)

Match the following Column-I (A) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CHO}\) (B) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) (B) \(\mathrm{HCHO}\) (D) \(\mathrm{CH}_{3} \mathrm{CHO}\) Column-II (p) Aldol addition (q) Cannizaro reaction (r) Perkin condensation (s) Haloform reaction (t) Positive test with Tollen's reagent

The total number of \(\beta\) - hydroxycarbonyl compounds which can be got by the aldol condensation of \(\mathrm{CH}_{3} \mathrm{CHO}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{CHO}\) is

The total number of enolates that can be formed, when 2- Butanone is treated with a base is

2,6 -octanedione is treated with alkali giving an aldol product. How many optically active isomer(s) is/are present in the final product?

With how many molecules of ammonia does formaldehyde condense to form urotropine?

\(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH} \frac{\mathrm{Cl}_{2}}{\text { red } \mathrm{P}} \rightarrow \mathrm{A} \stackrel{\text { alc. } \mathrm{KOH}}{\longrightarrow}\) B What is B? (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}\) (b) \(\mathrm{ClCH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCl}\) (d) \(\mathrm{CH}_{2}=\mathrm{CHCOOH}\)

When \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{COOH}\) is reduced with \(\mathrm{LiAlH}_{4}\) the compound obtained will be (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{COOH}\) (b) \(\mathrm{CH}_{2}=\mathrm{CH}-\mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3}^{2}-\mathrm{CH}_{2}-\mathrm{CH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}^{2}-\mathrm{CHO}\)

In the anion HCOO- the two carbon-oxygen bonds are found to be of equal length. What is the reason for it? (a) electronic orbits of carbon atom are hybridized (b) The \(\mathrm{C}=\mathrm{O}\) bond is weaker than the \(\mathrm{C}-\mathrm{O}\) bond (c) The anion HCOO- has two resonating structures (d) the anion is obtained by removal of a proton from the acid molecule

The general formula \(\mathrm{C}_{\mathrm{n}} \mathrm{H}_{2 \mathrm{n}} \mathrm{O}_{2}\) could be for open chain (a) carboxylic acid (b) diols (c) diketones (d) dialdehydes

The reaction [R]C(=O)C(N)=O \(+\mathrm{X} \odot\) is fastest when \(\mathrm{X}\) is (a) \(\mathrm{Cl}\) (b) \(\mathrm{NH}_{2}\) (c) \(\mathrm{OC}_{2} \mathrm{H}_{5}\) (d) OCOR

On mixing ethyl acetate with aqueous sodium chloride, the composition of the resultant solution is (a) \(\mathrm{CH}_{3} \mathrm{COOC}_{2} \mathrm{H}_{5}+\mathrm{NaCl}\) (b) \(\mathrm{CH}_{2} \mathrm{COONa}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{COCl}+\mathrm{C}_{2} \mathrm{H}_{s} \mathrm{OH}+\mathrm{NaOH}\) (d) \(\mathrm{CH}_{3} \mathrm{Cl}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{COONa}\)

Acetyl bromide reacts with excess of \(\mathrm{CH}_{3} \mathrm{MgI}\) followed by treatment with a saturated solution of \(\mathrm{NH}_{4} \mathrm{Cl}\) gives (a) acetone (b) acetamide (c) 2 -methyl-2-propanol (d) acetyl iodide

Which one of the following is reduced with zinc and hydrochloric acid to give the corresponding hydrocarbon? (a) ethyl acetate (b) acetic acid (c) acetamide (d) butan-2-one

Among the following acids which has the lowest pKa value? (a) \(\mathrm{CH}_{3} \mathrm{COOH}\) (b) \(\mathrm{HCOOH}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COH}\)

The best reagent to convert pent-3-en-2-ol into pent3-en \(-2\)-one is (a) acidic permanganate (b) acidic dichromate (c) chromic anhydride in glacial acetic acid (d) pyridinium chloro-chromate

Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a compound if water during the reaction is continuously removed. The compound formed is generally known as (a) a Schiff's base (b) an enamine (c) an imine (d) an amine

Reaction of cyclohexanone with dimethylamine in the presence of catalytic amount of an acid forms a compound if water during the reaction is continuously removed. The compound formed is generally known as (a) a Schiff's base (b) an enamine (c) an imine (d) an amine

Phenyl magnesium bromide reacts with methanol to give (a) a mixture of anisole and \(\mathrm{Mg}(\mathrm{OH}) \mathrm{Br}\) (b) a mixture of benzene and \(\mathrm{Mg}(\mathrm{OMe}) \mathrm{Br}\) (c) a mixture of toluene and \(\mathrm{Mg}(\mathrm{OH}) \mathrm{Br}\) (d) a mixture of phenol and \(\mathrm{Mg}(\mathrm{Me}) \mathrm{Br}\)

Among the following mixtures, dipole-dipole as the major interaction, is present in (a) benzene and ethanol (b) acetonitrile and acetone (c) \(\mathrm{KCl}\) and water (d) benzene and carbon tetrachloride

The correct order of increasing acid strength of the compound is (a) \(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\) (b) \(\mathrm{MeOCH}_{2} \mathrm{CO}_{2} \mathrm{H}\) (c) \(\mathrm{CF}_{3} \mathrm{CO}_{2} \mathrm{H}\) (d) \((\mathrm{Me})_{2} \mathrm{CH} \mathrm{CO}_{2} \mathrm{H}\) (a) \(\mathrm{b}<\mathrm{d}<\mathrm{a}<\mathrm{c}\) (b) \(\mathrm{d}<\mathrm{a}<\mathrm{c}<\mathrm{b}\) (c) \(\mathrm{d}<\mathrm{a}<\mathrm{b}<\mathrm{c}\) (d) \(a

A liquid was mixed with ethanol and a drop of concentrated \(\mathrm{H}_{2} \mathrm{SO}_{4}\) was added a compound with a fruity smell was formed. The liquid was: (a) HCHO (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{OH}\)