**Synthesis of 2-Phenylethanol from Benzene and Ethylene Oxide****Concept Overview:**2-phenylethanol, a molecule extensively used in perfumery, can be synthesized by treating benzene with ethylene oxide in the presence of a strong acid catalyst. This reaction involves the formation of a sigma complex intermediate.**Reaction Description:**The image illustrates the chemical reaction where benzene is treated with ethylene oxide, in the presence of protons ([H⁺]) as a catalyst, to produce 2-phenylethanol.**Reaction Components:**- **Reactants:** - Benzene: Represented as a hexagon with alternating double bonds. - Ethylene Oxide: A three-membered cyclic ether represented as a triangle with an oxygen atom at one vertex.- **Conditions:** - Presence of a strong acid catalyst ([H⁺]).- **Product:** - 2-phenylethanol: Shown as a benzene ring attached to a two-carbon chain with a hydroxyl group (OH) at the end.**Task:**Propose a mechanism for this reaction, illustrating all resonance forms of the sigma complex intermediate. The intermediate is crucial as it determines how the ethylene oxide interacts with the benzene ring, facilitated by the acid catalyst.

Preparation of 2-phenylethanol from benzene is proceed via electrophilic aromatic substitution…

2-phenylethanol, a molecule extensively used in perfumery, can be prepared by treating benzene with ethylene oxide in the presence of a strong acid catalyst. Propose a mechanism for this reaction, showing all resonance forms of the sigma complex intermediate. [H+] OH

2-phenylethanol, a molecule extensively used in perfumery, can be prepared by treating benzene with ethylene oxide in the presence of a strong acid catalyst. Propose a mechanism for this reaction, showing all resonance forms of the sigma complex intermediate. [H+] OH

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

See similar textbooks

Related questions

Q: 5a) Pd-catalyzed reaction Br OH CO, BU3N cat. Pd(OAc)₂ Ph3P

A: Pd can form organometallic reagents. The organometallic reagents Pd are majorly used as a catalyst…

Q: propose a mechanism--not the name of the mechanism, but showing electron movement-for following…

A: Given : structure of reactant and product Tip : E1 reaction will occur

Q: Br Br Mg ether + (CH3CH₂)₂CuLi OH PBr3 ether ether

A: One of the method which includes the alkylation of an organic compound is carried out by using…

Q: The reaction of N−bromosuccinimide with 4−methyl−3−nitroanisole has been reported in the chemical…

A: N- bromosuccinimide gives free radical substitution at allylic position.

Q: Predict the major products for each reaction. If there is more than one product indicate a relative…

A: The objective is to determine the product of the given reaction.

Q: (b) Reactivity with the SN1 by the treatment with NaOH

A: A question based on reactive intermediates. Based on the stability of the carbocation the reactivity…

Q: (c) Propose reagents and conditions for the following 3-step synthesis of secondary amine 10,…

A: We have find out the reagents and conditions for the 3-step synthesis of secondary amine.

Q: (a) _MgBr + O=C=O

A: In the first reaction, Phenyl magnesium bromide is reacting with carbon dioxide. In carbon dioxide,…

Q: 3 The UV−vis spectrum for K[VO(O2)Hheida] shows an absorption at 435 nm (ε = 4 × 102 M−1 cm−1). What…

A: Spectroscopy is based on the interaction between light and matter. The principle of UV-VIS…

Q: Provide the mechanism and product

Q: (0) + CN (†) O + O O

A: Diels-Alder reaction: It is a [4+2] cycloaddition reaction between a diene and dienophile to give a…

Q: Predict the products of the following reactions: (a) (b) (c) O O CI + NaOH OCH 3 NH₂ + NaOH + NaCl

A: Given reactions are : Predict the products of the reaction ?

Q: a) Propose an efficient synthesis for the following reaction: b) Write the mechanism and predict the…

A: The conversion of a reactant to a desired product requires the chemical reaction of that reactant…

Q: You are given a mixture of the compounds shown below. Which of these compounds would you be able to…

A: Step 1:

Q: H2SO4 LOH HBr 2) OH

A: On reaction of alcohol with H2SO4, dehydration of alcohol takes place producing alkene via…

Q: lodify the structure of the compound provided to show the skeletal structure of the product that…

A: on reaction with K2Cr2O7, secondary alcohol (RCH(OH)R') gets oxidized to ketone (RCOR') and aldehyde…

Q: Treating a Grignard reagent with carbon dioxide followed by aqueous HCI gives a car- boxylic acid.…

Q: Propose products (if any) and mechanisms for the following AlCl3-catalyzed reactions:…

A: The details solution for this is provided below in step II.

Q: Provide the mechanism for the following transformation: NaCN CN + Naci

Q: Give the starting material and mechanism arrows needed to produce the given product by coordination.…

A: reaction mechanism is the sequence of elementary steps by which a chemical reaction occurs.

Q: NH,NH2 of `NHNH2 pyridine H20 -ОН HO

A: The first reaction given is the reaction of acid chloride with hydrazine and the second reaction…

Q: Ethylene oxide is the starting material for the synthesis of Cellosolve, an important industrial…

Q: Br OH 45°C +HO a higher temperature favors elimination + H₂O + Br 47% 53% Br OH 100 °C + HO¯ + + H₂O…

A: The objective of the question is to understand the effect of temperature on the reaction of BrOH…

Q: + HCI CI Br + HBr

A: Electrophilic addition of a hydrohalic acid to a double bond usually occurs through a carbocationic…

Q: Give the mechanisms for the following:

Q: Benzene can be hydroxylated by treating it with hydrogen peroxide and a strong acid such as…

A: Given reaction:

Q: Choose the correct statement(s) regarding Aryl halides participation in Transition metal catalyzed…

Q: + O

Q: Provide synthetic routes for the preparation of the starting materials of azo dye Alizarine Yellow R…

A: Given are organic synthesis reactions.The given compounds are starting compounds of atoms dye…

Q: Predict the products of the following reactions: O (a) (b) (c) O O CI + NaOH OCH 3 NH₂ + NaOH + NaCl

A: There are some of the given reactions describing the reaction of different nucleophiles with several…

Q: (a) NC CN (b) + NC CN

A: Diels-Alder reaction: It is a [4+2] cycloaddition reaction between a diene and dienophile to give a…

Q: LNe Peagent list, identify the reagent needed for each transformation below. The reagent list is in…

Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

**Synthesis of 2-Phenylethanol from Benzene and Ethylene Oxide**

**Concept Overview:**
2-phenylethanol, a molecule extensively used in perfumery, can be synthesized by treating benzene with ethylene oxide in the presence of a strong acid catalyst. This reaction involves the formation of a sigma complex intermediate.

**Reaction Description:**
The image illustrates the chemical reaction where benzene is treated with ethylene oxide, in the presence of protons ([H⁺]) as a catalyst, to produce 2-phenylethanol.

**Reaction Components:**
- **Reactants:**
- Benzene: Represented as a hexagon with alternating double bonds.
- Ethylene Oxide: A three-membered cyclic ether represented as a triangle with an oxygen atom at one vertex.

- **Conditions:**
- Presence of a strong acid catalyst ([H⁺]).

- **Product:**
- 2-phenylethanol: Shown as a benzene ring attached to a two-carbon chain with a hydroxyl group (OH) at the end.

**Task:**
Propose a mechanism for this reaction, illustrating all resonance forms of the sigma complex intermediate. The intermediate is crucial as it determines how the ethylene oxide interacts with the benzene ring, facilitated by the acid catalyst.

Expert Solution

This question has been solved!

Explore an expertly crafted, step-by-step solution for a thorough understanding of key concepts.

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Step by step

Solved in 2 steps with 1 images

SEE SOLUTION Check out a sample Q&A here

Knowledge Booster

Learn more about

Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.

Similar questions

Compound X, shown below, spontaneously reacts via an intramolecular SN2 to produce intermediate Y, known as an "aziridinium" ion. In the presence of water, intermediate Y reacts further to form product Z. What is the identity of product Z. OH (A) + En Br O (B) aziridinium ion Y OH (C) H₂O + En Z HO
Predict the product of the following reactions
• What is the role of saccharin in the reaction? Show reaction. ● What compound was used to couple with the diazonium? Show the reaction. Is it regiospecific/regioselective? Explain. Sac and HOAC 1-Bu -Bu N -BUOH [NONEO] Ho Ar-NEN Sac and HOAC Ar-NH, Ar N²0 OH N+O: -H₂O 1(a-1) Ar-N=N 2(0-1) Ar-NEN: -H CHO CHO 3(-1) Scheme 2: The diazotization process of aryl amines in presence of saccharin and tert-butyl nitrite, followed by azo coupling reaction with 4-hydroxybenzaldehyde. IN=0:- COH O NIN + OH CHO
Please show the mechanism of the chemical reaction to get from a benzene to a nitrobeneze to aniline
propose a mechanism for the following reaction:
10-Bromo-a-chamigrene, a compound isolated from marine algae, is thought to be biosynthesized from y-bisabolene by the following route: "Br* Bromonium Cyclic carbocation -H*) Base ion Bromo peroxidase Br y-Bisabolene 10-Bromo-a- chamigrene
1. Give products for the following reactions. EtO NH₂
Which compounds must be reacted to generate the indicated products?