ORGANIC CHEMISTRY-ETEXT REG ACCESS
ORGANIC CHEMISTRY-ETEXT REG ACCESS
12th Edition
ISBN: 9781119308362
Author: Solomons
Publisher: WILEY
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Chapter 6, Problem 30P
Interpretation Introduction

Interpretation:

The reaction mechanism that accounts for the products of the given reactions is to be written.

Concept Introduction:

▸ Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.

▸ Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.

▸ Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

▸ Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.

SN2 reaction is the nucleophilic substitution reaction in which the two components are involved in the rate determining step.

▸ The SN2 mechanism of substitution reaction occurs in secondary alkyl halides with an inversion of configuration.

▸ The SN2 reaction takes place in one step. The nucleophile attacks the alkyl halide from the side opposite to the leaving group, resulting in an inversion of configuration.

▸ An SN1 reaction is a nucleophilic substitution reaction in which only one component is involved in the rate-determining step.

▸ The nucleophilic substitutions in which a nucleophile replaces a leaving group are known as SN1 reactions.

SN1 reactions are unimolecular as the rate of reaction is dependent on the concentration of a single reactant.

▸ Carbocation is a molecule having a carbon atom bearing three bonds and a positive formal charge.

▸ Carbocation are generally unstable because they do not have eight electrons to satisfy the octet rule.

▸ The order of stability of carbocation is such that the tertiary carbocation is the most stable whereas the primary carbocation is the least stable, and secondary carbocation lies between primary and tertiary carbocations.

▸ If primary carbocation is obtained in product, it rearranges itself to secondary or tertiary carbocation to form more stable product.

▸ If secondary carbocation is obtained in product, it rearranges itself to tertiary carbocation to form more stable product.

▸ The stability of carbocation: 3ocarbocation>2ocarbocation>1ocarbocation>methylcarbocation

SN2 reaction is the nucleophilic substitution reaction in which two components are involved in the rate determining step.

SN1 reaction is the nucleophilic substitution reaction in which only one component is involved in the rate determining step.

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A J то گای ه +0 Also calculate the amount of starting materials chlorobenzaldehyde and p-chloroacetophenone required to prepare 400 mg of the given chalcone product 1, 3-bis(4-chlorophenyl)prop-2-en-1-one molar mass ok 1,3-bis(4-Chlorophenyl) prop-2-en-1-one = 277.1591m01 number of moles= 0.400/277.15 = 0.00144 moles 2 x 0.00 144=0.00288 moves arams of acetophenone = 0.00144 X 120.16 = 0.1739 0.1739x2=0.3469 grams of benzaldehyde = 0.00144X106.12=0.1539 0.1539x2 = 0.3069 Starting materials: 0.3469 Ox acetophenone, 0.3069 of benzaldehyde 3
1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.
3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in the reactant before being able to draw the arrows corresponding to product formation. A. B. Rearrangement ΘΗ
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