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Chapter 6: Problem 148

Which of the following compounds reacts with benzaldehyde to form a product containing \(\backslash \mathrm{C}=\mathrm{N}\) ? (a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (c) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NHNH}_{2}\) (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}\left(\mathrm{CH}_{3}\right)_{2}\)

Short Answer

Expert verified
a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\) b) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NH}_2\) c) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NHNH}_2\) d) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}\left(\mathrm{CH}_3\right)_2\) Answer: c) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NHNH}_2\) (phenylhydrazine)

Step by step solution

01

(a) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{NH}\)

This compound is a secondary amine, and it can react with benzaldehyde, but it would form an imine rather than the desired product containing C=N. Imines are formed when carbonyl compounds react with primary amines, so this compound is not the correct choice.
02

(b) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NH}_2\)

This compound is aniline, which is a primary amine. When benzaldehyde reacts with a primary amine, it forms an imine, not the desired product containing a C=N bond. Therefore, this compound is not the correct choice.
03

(c) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NHNH}_2\)

This compound is phenylhydrazine, which contains an \(\mathrm(NH-NH_2)\) fragment. When benzaldehyde reacts with phenylhydrazine, it forms the corresponding hydrazone via a carbon-nitrogen double bond (C=N). Therefore, this compound can react with benzaldehyde to form the desired product containing the C=N bond.
04

(d) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{~N}\left(\mathrm{CH}_3\right)_2\)

This compound is N,N-dimethylaniline, which is a tertiary amine. Tertiary amines do not react with benzaldehyde to form a product containing a C=N bond, so this compound is not the correct choice. Based on the analysis, the correct answer is:
05

Answer

(c) \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{NHNH}_2\) (phenylhydrazine)

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Most popular questions from this chapter

This section contains multiple choice questions. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. The structure of the product formed when cyclohexanone reacts with dimethylamine in presence of catalytic amount of an acid such as \(\mathrm{p}\) -toluene sulphonic acid is

Identify the reactions in which both the nitrogen atoms of benzene diazonium chloride are retained in the product. (a) Reduction with zinc and hydrochloric acid (b) Reduction with \(\mathrm{SnCl}\), and hydrochloric acid (c) Reduction with sodium sulphite (d) Coupling reaction

How are the following conversions carried out? (i) Ethyl amine to methyl amine (ii) Benzene to phenyl hydrazine (iii) meta dinitrobenzene to meta bromo phenol

Directions: This section contains 3 paragraphs. Based upon the paragraph, 3 multiple choice questions have to be answered. Each question has 4 choices (a), (b), (c) and (d), out of which ONLY ONE is correct. Passage I Amines have the formula \(\mathrm{RNH}_{2}\) and can be prepared by different methods. Some of them are (i) reduction of nitriles (ii) reduction of amides (iii) reduction of azides and (iv) Gabriel phthalimide synthesis. The most important property of amines is their basicity due to the presence of lone pair of electrons on nitrogen. Answer the following questions. The method, \(\mathrm{RX} \stackrel{\mathrm{KCN}}{\longrightarrow} \mathrm{RCN}, \frac{\text { (i) LiAlH }_{4} \text { lether }}{\text { (ii) } \mathrm{H}_{2} \mathrm{O}} \mathrm{RCH}_{2} \mathrm{NH}_{2}\) is not suitable for the preparation of benzyl amine because (a) \(\mathrm{RX} \stackrel{\mathrm{KCN}}{\longrightarrow} \mathrm{RCN}\) reaction is not possible since chlorobenzene does not undergo \(\mathrm{S}_{\mathrm{N}} 1\) or \(\mathrm{S}_{\mathrm{N}} 2\) reaction. (b) It is difficult to reduce \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CN}\) to \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (c) Bromobenzene gets oxidized (d) LiAlH \(_{4}\) cannot reduce \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CN}\).

The BS reading at \(A\) is \(2.355 \mathrm{~m}\) and the fore sight reading at \(B\) is \(1.505 \mathrm{~m}\). Find the level difference between \(A\) and \(B\).
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