Chapter 28

A and B react with Na gives \(\mathrm{H}_{2}\) gas and by reaction of both \(\mathrm{A}\) and \(\mathrm{B}\) ethyl acetate is formed then \(\mathrm{A}\) and \(\mathrm{B}\) are (a) \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (b) \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{CH}_{3} \mathrm{OH}\) (c) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{COOH}, \mathrm{C}_{3} \mathrm{H}_{7} \mathrm{OH}\) (d) \(\mathrm{HCOOH}, \mathrm{CH}_{3} \mathrm{COOH}\)

Carboxylic acid undergoes ionization due to (a) hydrogen bonding (b) absence of \(\alpha\)-hydrogen (c) high reactivity of \(\alpha\)-hydrogen (d) resonance stabilization of carboxylate ions

Benzoyl chloride is prepared from benzoic acid by (a) \(\mathrm{Cl}_{2}, \mathrm{hv}\) (b) \(\mathrm{SO}_{2} \mathrm{Cl}_{2}\) (c) \(\mathrm{SOCl}_{2}\) (d) \(\mathrm{Cl}_{2}, \mathrm{H}_{2} \mathrm{O}\)

Which reagent will bring about the conversion of carboxylic acid into esters? (a) Dry \(\mathrm{HCl}+\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (b) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) (c) \(\mathrm{LiAlH}_{4}\) (d) \(\mathrm{Al}\left(\mathrm{OC}_{2} \mathrm{H}_{3}\right)_{3}\)

In an \(\alpha\)-halogenation of aliphatic acids (HVZ reaction) the catalyst used is (a) \(\mathrm{AlCl}_{3}\) (b) \(\mathrm{P}\) (c) \(\mathrm{Zn}\) (d) \(\mathrm{FeCl}_{3}\)

The fatty acid which shows reducing property is (a) ethanoic acid (b) oxalic acid (c) formic acid (d) acetic acid

A compound of molecular weight 180 is acetylated to give a compound of molecular weight \(390 .\) The number of amino groups in the compound is (a) 6 (b) 5 (c) 4 (d) 3

The work of concentration. \(\mathrm{H}_{2} \mathrm{SO}_{4}\) in esterification process is as (a) dehydrating agent and catalyst (b) dehydrating agent

Formic acid and acetic acid can be distinguished chemically by (a) reaction with HCl (b) iodoform test (c) reaction with \(\mathrm{NH}_{3}\) (d) reaction with \(\mathrm{FeCl}_{3}\) solution

\(\mathrm{CH}_{3} \mathrm{COCl}\) reacts with (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) Salicylic acid (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}\) (d) all of these

What will happen if \(\mathrm{LiAlH}_{4}\) is added to an ester? (a) one unit of alcohol and one unit of acid is obtained (b) two units of alcohol are obtained (c) two units of acids are obtained (d) none of these

A fruity smell is produced by the reaction of \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{OH}\) with (a) \(\mathrm{PCl}_{5}\) (b) \(\mathrm{CH}_{3} \mathrm{COOH}\) (c) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (d) none of these

Which of the following formula is more reactive for hydrolysis? (a) \(-\mathrm{COOR}\) (b) \(-\mathrm{CONH}_{2}\) (c) \(-\mathrm{COOH}\) (d) \(-\mathrm{COCl}\)

In the mechanism of Hoffimann reaction, which intermediate rearranges to alkyl isocyanate? (a) nitrene (b) amide (c) nitroso (d) bromamide

Here the strongest acid is (a) \(\mathrm{CH}_{3}-\mathrm{COOH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{COOH}\) (c) \(\mathrm{Cl}-\mathrm{CH}_{2}-\mathrm{COOH}\) (d) \(\mathrm{Br}-\mathrm{CH}_{2}-\mathrm{COOH}\)

Identify the wrong statement from the following: 8 (a) methyl salicylate is an ester (b) salicylic acid is a monobasic acid (c) methyl salicylate does not occur in natural oils (d) salicylic acid gives violet colour with neutral ferric chloride as well as brisk effervescence with sodium bicarbonate.

Which compound gives \(\mathrm{CO}_{2}\) with \(\mathrm{NaHCO}_{3} ?\) (a) hexanol (b) phenol + acetic acid (c) \(\mathrm{n}\)-butanol (d) acetic acid

On strong heating, ammonium acetate gives (a) urea (b) formamide (c) acetamide (d) methyl cyanide

Which one of the following statements is incorrect? Benzaldehyde can be produced by the (a) reduction of benzoyl chloride (b) oxidation of toluene (c) hydrolysis of benzal chloride (d) reduction of benzyl chloride

What is the main reason for the fact that carboxylic acids can undergo ionization? (a) Resonance stabilization of the carboxylate ion (b) Hydrogen bonding (c) Absence of alpha hydrogen (d) High reactivity of alpha hydrogen

Which one of the following acids is thermally most unstable? (a) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{COOH}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (c) \(\mathrm{CH}_{3} \mathrm{COCOOH}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{2} \mathrm{CH}, \mathrm{COOH}\)

When propanamide reacts with \(\mathrm{Br}_{2}\) and \(\mathrm{NaOH}\) then which of the following compounds is formed? (a) propyl alcohol (b) ethyl alcohol (c) ethylamine (d) propylamine

Conversion of acetaldehyde into ethyl acetate in presence of aluminium ethoxide is called (a) Tischenko reaction (b) aldol condensation (c) Benzoin condensation (d) Cope reaction

Which reaction product is formed from benzaldehyde and methyl amine? (a) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}=\mathrm{NCH}_{3}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CONH}_{2}\)

Treatment of propionaldehyde with dil. \(\mathrm{NaOH}\) solution gives (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHOHCH}_{2} \mathrm{CH}_{2} \mathrm{CHO}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHOHCH}\left(\mathrm{CH}_{3}\right) \mathrm{CHO}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Identify the final product in the following sequence of reactions. $$ \begin{aligned} &\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{MgBr} \stackrel{\mathrm{CH}_{2}-\mathrm{CH}_{2}}{\mathrm{Mg}} \rightarrow(\mathrm{a}) \stackrel{\mathrm{H}_{3} \mathrm{O}^{+}}{\longrightarrow} \text { (b) } \\ &\stackrel{\mathrm{KMnO}_{4}}{\longrightarrow}(\mathrm{c}) \end{aligned} $$ (a) \(\mathrm{CH}_{3} \mathrm{CH}\left(\mathrm{CH}_{3}\right) \mathrm{COOH}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COOH}\)

Identify (a) in the following sequence of reactions. $$ \mathrm{C}_{4} \mathrm{H}_{7} \mathrm{OCl}(\mathrm{a}) \stackrel{\mathrm{NH}_{5}}{\longrightarrow} \mathrm{C}_{4} \mathrm{H}_{9} \mathrm{ON} \stackrel{\mathrm{Br}_{2}+\mathrm{NaOH}}{\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}} $$ (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COCl}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHClCHO}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{Cl}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{COCH}_{2} \mathrm{Cl}\)

$$ \mathrm{Br}-\left(\mathrm{CH}_{2}\right)_{4}-\mathrm{COOH} \frac{\text { (1) } \mathrm{OH}^{-}}{\left(\text {2) } \mathrm{H}^{+}\right.}{\longrightarrow} ? $$

Formaldehyde gives an additive product with meth ylmagnesium iodide which on aqueous hydrolysis gives (a) methyl alcohol (b) isopropyl alcohol (c) propyl alcohol (d) ethyl alcohol

During reduction of carbonyl compounds by hydrazine and KOH, the first intermediate formed is (a) \(\mathrm{RCH}=\mathrm{NH}\) (b) \(\mathrm{RCONH}_{2}\) (c) \(\mathrm{RCH}=\mathrm{NNH}_{2}\) (d) \(\mathrm{RC} \equiv \mathrm{N}\)

The reaction of benzaldehdye with alkali gives (a) benzene + benzyl alcohol (b) phenol + benzene (c) benzene \(+\) benzyl alcohol (d) benzyl alcohol + sodium benzoate

The cyanohydrin of a compound \(\mathrm{X}\) on hydrolysis gives lactic acid; the \(\mathrm{X}\) is (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}\) (b) \(\mathrm{CH}_{3} \mathrm{CHO}\) (c) \(\mathrm{HCHO}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{CHO}\)

Which of the following products is formed when benzaldehyde is treated with \(\mathrm{CH}_{3} \mathrm{MgBr}\) and the addition product so obtained is subjected to acid hydrolysis? (a) a primary alcohol (b) phenol (c) secondary alcohol (d) tert-Butyl alcohol

From which of the following tertiary butyl alcohol is obtained by the action of methyl magnesium iodide? (a) \(\mathrm{CO}_{2}\) (b) \(\mathrm{HCHO}\) (c) \(\mathrm{CH}_{3} \mathrm{CHO}\) (d) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\)

A substance \(\mathrm{C}_{4} \mathrm{H}_{10} \mathrm{O}\) yields on oxidation a compound, \(\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}\) which gives an oxime and a positive iodoform test. The original substance on treatment with conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}\) gives \(\mathrm{C}_{4} \mathrm{H}_{\mathrm{g}}\). The structure of the compound is (a) \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (b) \(\mathrm{CH}_{3} \mathrm{CHOHCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{O}-\mathrm{CH}_{2} \mathrm{CH}_{3}\)

In the reaction $$ \mathrm{CH}_{3} \mathrm{CHO}+\mathrm{CH}_{2}(\mathrm{COOH})_{2} \stackrel{\Delta, \text { Pyridine }}{\longrightarrow} \mathrm{A} $$ The compound \(\mathrm{A}\) is (a) \(\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCOOH}\) (b) \(\mathrm{COOHCH}=\mathrm{CHCOOH}\) (c) \(\mathrm{CH}_{3} \mathrm{COOH}\) (d) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{COOH}\)

$$ \left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO} \underset{(\mathrm{HCl})}{\stackrel{\mathrm{NaCN}}{\longrightarrow} \mathrm{A}} \stackrel{\mathrm{H}_{3} \mathrm{O}+}{\longrightarrow} \mathrm{B} $$ in the above sequence of reactions \(\mathrm{A}\) and \(\mathrm{B}\) are (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CN},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHCOOH}\) (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CN},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH})_{2}\) (c) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CN},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{COOH}\) (d) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CN},\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}=\mathrm{O}\)

The most reactive compound towards formation of cyanohydrin on treatment with KCN followed by acidification is (a) p-nitrobenzaldehyde (b) p-hydroxybenzaldehyde (c) benzaldehyde (d) phenylacetaldehyde

If 3 -hexanone is reacted with \(\mathrm{NaBH}_{4}\) followed by hydrolysis with \(\mathrm{D}_{2} \mathrm{O}\), the product will be (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CD}(\mathrm{OD}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OD}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CD}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\)

Which one of the following pairs is not correctly matched? (a) \(>\mathrm{C}=\mathrm{O} \longrightarrow \mathrm{CH}_{2}\) Clemmensen reduction (b) \(-\mathrm{COCl} \longrightarrow-\mathrm{CHO}\) Rosenmund reduction (c) \(>\mathrm{C}=\mathrm{O} \longrightarrow \mathrm{CHOH}\) Wolff - Kishner reduction (d) \(-\mathrm{C} \equiv \mathrm{N} \longrightarrow \mathrm{CHO}\) Stephen reduction

Which alkene is formed from the following yield carbonyl pair? \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}=\mathrm{PPh}_{3}+2\)-butanone (a) 1-methyl-5-methane (b) 3 -methyl-3-heptene (c) 4 -methyl-3-heptene (d) 5 -methyl-3-heptene

Predict the product 'B' in the sequence of reaction $$ \mathrm{HC} \equiv \mathrm{CH} \frac{30 \% \mathrm{H}_{2} \mathrm{SO}_{4}}{\mathrm{HgSO}_{4}}-\mathrm{A} \stackrel{\mathrm{NaOH}}{\mathrm{CH}} $$

An organic compound 'A' has the molecular formula \(\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O} .\) It undergoes iodoform test. When saturated with HCl it gives 'B' of molecular formula \(\mathrm{C}_{9} \mathrm{H}_{14} \mathrm{O}\). 'A' and ' \(\mathrm{B}\) ' respectively are (a) Propanone and 2,6 -dimethyl-2, 5 -heptadien-4-one (b) propanone and mesitylene oxide (c) propanal and mesitylene (d) propanol and mesityl oxide

Cinnamic acid is formed when \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CHO}\) condensation with \(\left(\mathrm{CH}_{3} \mathrm{CO}\right)_{2} \mathrm{O}\) in presence of (a) sodium metal (b) sodium acetate (c) anhydrous \(\mathrm{ZnCl}_{2}\) (d) conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}\)

A compound gives a yellow ppt. on warming with the aqueous solution of \(\mathrm{NaOH}\). Its vapour density is 29 . The compound is (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}\) (b) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CHOHCH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}\)

In the reaction \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C} \equiv \mathrm{CH} \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4}, \mathrm{HgSO}_{4}}{\longrightarrow}[\mathrm{A}]\) The compound [A] is (a) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{COOH}\) (b) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CH}_{2}-\mathrm{CHO}\) (c) \(\mathrm{CH}_{3}-\mathrm{CH}_{2}-\mathrm{CO}-\mathrm{CH}_{3}\) (d) none of these

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 smallest ketone and its next homologue are reacted with \(\mathrm{NH}_{2} \mathrm{OH}\) to form oxime then (a) two different oximes are formed (b) three different oximes are fomed (c) two oximes are optically active (d) all oximes are optically active

A mixture of benzaldehyde and formaldehyde on heating with aqueous \(\mathrm{NaOH}\) solution gives (a) benzyl alcohol and sodium formate (b) sodium benzoate and methyl alcohol (c) sodium benzoate and sodium formate (d) benzyl alcohol and methyl alcohol

In the Cannizzaro reaction given below, \(2 \mathrm{Ph}-\mathrm{CHO} \stackrel{\mathrm{OH}}{\longrightarrow} \mathrm{Ph}-\mathrm{CH}_{2} \mathrm{OH}+\mathrm{PhCO}_{2}^{-}\) the slowest step is (a) the attack of \(-\mathrm{OH}\) at the carbonyl group (b) the transfer of hydride ion to the carbonyl group (c) the abstraction of proton from the carboxylic acid (d) the deprotonation of \(\mathrm{Ph}-\mathrm{CH}_{2} \mathrm{OH}\).