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Chapter 2: Problem 5

(a) Write the structure of organic product formed by heating \(\mathrm{C}\left(\mathrm{CH}_{2} \mathrm{I}\right)_{4}\) with zinc dust. (b) How is buta- 1,3 -diene prepared from but- 1 -ene (c) What are the products expected when ethylene is passed into an aqueous solution of bromine containing dissolved sodium chloride?

Short Answer

Expert verified
Short Answer: (a) The organic product formed by heating C(CH2I)4 with zinc dust is C(CH2I)3-CH2-C(CH2I)3, which results from a Wurtz coupling reaction. (b) To prepare buta-1,3-diene from but-1-ene, halogenate but-1-ene to form 1,2-dihalobutane and perform dehydrohalogenation using a strong base like KOH, resulting in CH2=CH-CH=CH2. (c) When ethylene is passed into an aqueous solution of bromine containing dissolved sodium chloride, 1,2-dibromoethane (CH2Br-CH2Br) is formed through an electrophilic addition reaction.

Step by step solution

01

Problem (a): Determine the product of the reaction with zinc dust.

In this problem, we have to find the organic product formed by heating C(CH2I)4 with zinc dust. The reaction is known as Wurtz reaction in which zinc is used instead of sodium. This is a coupling reaction involving the formation of a new carbon-carbon bond. To perform this step-by-step, we need to: 1. Write the structure of C(CH2I)4 2. Perform the coupling reaction using zinc dust 3. Write the structure of the organic product formed
02

Write the structure of C(CH2I)4

C(CH2I)4 can be written as the following structure: CI-CH2-C(CH2I)3 The central carbon is attached to three CH2I groups.
03

Perform the coupling reaction using zinc dust

When the compound is heated with zinc dust, zinc replaces iodine and forms zinc iodide, and the carbon atoms are joined together to form a new carbon-carbon bond. The reaction can be represented as follows: 2C(CH2I)4 + Zn → 2C(CH2I)3-CH2- - Zinc iodide
04

Write the structure of the organic product formed

The structure of the organic product formed after the coupling reaction can be written as: C(CH2I)3-CH2-C(CH2I)3
05

Problem (b): Preparation of buta-1,3-diene from but-1-ene.

To prepare buta-1,3-diene from but-1-ene, we need to perform these steps: 1. Write the structure of but-1-ene 2. Perform dehydrohalogenation using a strong base 3. Write the structure of buta-1,3-diene
06

Write the structure of but-1-ene

But-1-ene is an alkene with the following structure: CH2=CH-CH2-CH3
07

Perform dehydrohalogenation using a strong base

To prepare buta-1,3-diene from but-1-ene, first, we need to halogenate the but-1-ene to form 1,2-dihalobutane. Then, by using a strong base like an alkoxide base or KOH, we perform the dehydrohalogenation to form buta-1,3-diene. The reactions can be represented as follows: CH2=CH-CH2-CH3 + Br2 → CH2Br-CHBr-CH2-CH3 CH2Br-CHBr-CH2-CH3 + 2KOH → CH2=CH-CH=CH2 + 2KBr + 2H2O
08

Write the structure of buta-1,3-diene

The structure of buta-1,3-diene can be written as: CH2=CH-CH=CH2
09

Problem (c): Products when ethylene is passed into an aqueous solution of bromine containing dissolved sodium chloride.

To find the products of the given reaction, we need to perform these steps: 1. Write the structure of ethylene 2. Write the reaction of ethylene with bromine and sodium chloride 3. Write the structure of the products formed
10

Write the structure of ethylene

Ethylene is an alkene with two carbon atoms and a double bond between them. Its structure can be written as: CH2=CH2
11

Write the reaction of ethylene with bromine and sodium chloride

When ethylene is passed into an aqueous solution of bromine containing dissolved sodium chloride, bromine reacts with ethylene in an electrophilic addition reaction to form 1,2-dibromoethane. The reaction can be represented as follows: CH2=CH2 + Br2 → CH2Br-CH2Br
12

Write the structure of the products formed

The structure of the product formed in this reaction is 1,2-dibromoethane, which can be written as: CH2Br-CH2Br

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Most popular questions from this chapter

Directions: Each question contains Statement-1 and Statement-2 and has the following choices (a), (b), (c) and (d), out of which ONLY ONE is correct. (a) Statement- 1 is True, Statement- 2 is True; Statement- 2 is a correct explanation for Statement-1 (b) Statement- 1 is True, Statement- 2 is True; Statement- 2 is NOT a correct explanation for Statement-1 (c) Statement-1 is True, Statement- 2 is False (d) Statement- 1 is False, Statement- 2 is True Statement 1 Oxymercuration reduction of an alkene gives an alcohol in which the -OH group is added to a more branched carbon of the double bond, while hydroboration- oxidation of an alkene gives an alcohol in which the -OH group is added to a less branched carbon of the alkene. and Statement 2 Hydration of an alkene in the presence of an acid is one of the standard methods of preparation of an alcohol form alkenes.

The number of structural and stereoisomers of a bromo compound \(\mathrm{C}_{5} \mathrm{H}_{9} \mathrm{Br}\) formed by the addition of \(\mathrm{HBr}\) to pent- 2 yne are respectively (a) 4 and 2 (b) 1 and 2 (c) 2 and 4 (d) 2 and 1

Simplest alkane which can exhibit optical activity is (a) 3 -methyl hexane (b) 3 -methyl heptane (c) 2 -methyl butane (d) neopentane

The reagent that does not react with ethyne is (a) Ammoniacal \(\mathrm{AgNO}_{3}\) (b) \(\mathrm{NaOH}\) (c) \(\mathrm{HCl}\) (d) Na

A reaction in which an alkene is formed is (a) 1 -bromo-1-methylcyclohexane is treated with \(\mathrm{NaOH}\) in the presence of acetone. (b) 1 -bromo- 1 -methylcyclohexane is treated with \(\left(\mathrm{C}_{2} \mathrm{H}_{5}\right)_{3} \mathrm{~N}\). (c) Chlorocyclohexane is heated with \(\left(\mathrm{CH}_{3}\right)_{3}\) CONa in t-butanol (d) 1 -bromo-1-phenylbutane is treated with aqueous \(\mathrm{NaOH}\)
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