Draw the complete mechanism of the ring opening of the epoxide below with methanol under both acidic and basic conditions. Based on your mechanisms, explain both the regiochemistry and stereochemistry observed in the products. CH,O CH,OH cat. HA CH,OH

Draw the complete mechanism of the ring opening of the epoxide below with methanol under both acidic and basic conditions. Based on your mechanisms, explain both the regiochemistry and stereochemistry observed in the products. CH,O CH,OH cat. HA CH,OH

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 12CTQ

See similar textbooks

Related questions

Q: 2a. Draw the mechanism and major product of the synthesis reaction below. b. Give the reagent(s)…

A: Given reaction is, E1 reaction I.e. unimolecular elimination reaction.

Q: Which statement best describes what is happening in step 6? (Remember, this is copied from the full…

A: In the given step left side one is imine. Imine is converted to examine through tautomerisation

Q: Give a clear handwritten answer..... give the mechanism of given bleow reactions ....

Q: a) b) HO, HO c) OH Br

A: The cyclohexanecarbaldehyde will firstly reduce to alcohol via a reducing agent. The reducing agent…

Q: 2. Show the B-cleavage mechanism and product for following reaction -R R'

A: The given problem deals with β - cleavage reactions which are generally initiated in the presence of…

Q: which substrates undergo a carbocation rearrangement in an SN1 mechanism?

A: The SN1 mechanism has 2 steps - 1- formation of carbocation 2- attack of nucleophile

Q: Draw the structures for the intermediates and product (left to right) as represented by A to C in…

A: In this question we have to tell the product of the reaction sequence.

Q: Consider the intramolecular nucleophilic substitution reaction shown here. Does the stereochemistry…

A: The given intramolecular nucleophilic substitution reaction is,

Q: 4. Show the mechanism for the interconversion of the compounds below. Hint: They go through a…

A: In the presence of base acetone make enolate. Enolate acts as anucleophile and undergoes Michael…

Q: Write a detailed mechanism for the following reaction. OEt H -OEt 2 ELOH

Q: Which statement best describes what is happening in step 5? (Remember, this is copied from the ful…

A: The reaction given is,

Q: Provide the mechanism for the 4th and final reaction in this synthesis: КОН/D20 D FHN- OH

A: Answer

Q: Now that we have synthesized the required aldehyde, the synthesis of ketone A can be accomplished,…

A: Given: Reaction. To find : Suitable Reagents. Solution: At first the Alkene attacks on carbonyl…

Q: Give the major product of the following reaction. MeO H2

A: Given,

Q: H2NNH2 'NH R-N N-R NH cat. H+

Q: In a unimolecular elimination (E1) reaction, the correct order of mechanistic steps is А.…

A: E1 Mechanism Proceeds through loss of a eaving group (LG) and then deprotonation.

Q: Propose a mechanism for the following reaction:

A: A Grignard reagent is an organomagnesium compound which can be described by the chemical formula…

Q: Show the complete mechanism for the reaction of t-butyl bromide with water to produce…

A: Given :- t-butyl bromide + water → 2-methyl-2-propanol To draw :- Complete mechanism of reaction

Q: Can someone draw the entire mechanism with arrows for this reaction? I am mainly confused regarding…

A: The mechanism have Elimination and Substitution Reactions both .

Q: Devise a detailed mechanism for formation of the major product of the elimination reactie он CH3…

A: An elimination reaction is a type of organic reaction in which two substituents are removed from a…

Q: Praetice Give a mechanism that is the reverse of the following reaction: H20

A: The reverse reaction steps are

Q: (e) Draw the structure of the iminium intermediate for the following transformation, and show the…

A: Interpretation - To draw the structure of the iminium ion intermediate for the following reaction…

Q: HO NH2 H3O+ HO NH HO Но

A: 4-(2-aminoethyl)bnzene-1,2 diol reacts with acetaldehyde in the presence of acid, it results in the…

Q: Propose a mechanism for the following reaction that explains why the configuration of the asymmetric…

A: In the above mechanism, the diazonium compound is offensive by electron-rich substrates. The…

Q: 5. Provide a mechanism for the following transformation: H2SO4 ÓH

A: We have to predict the mechanism for given reaction.

Q: Show the complete mechanism for the formation of the major product(s) for the following reaction?…

A: The reaction follows free radical mechanism:

Q: Draw curved arrows to illustrate the mechanism for the reaction of 3‑methylbutan‑1‑ol and HBrHBr.…

Q: NaOH (аc) Ph NaOH (ac) Ph O Na CHI3 1. Ph 12 H20

A: The reaction taking place is given as,

Q: Illustrate detailed mechanisms and draw Product Z that could be obtained from the reaction belo +…

Q: 6

A: First mercuration of alkene will happen.

Q: OCH3 + CH3B H;CO OCH3 H;CO OCH3 ČH3

A: Welcome to bartleby!

Q: H3C CH3 H3C CH3 Br NaH H.

A: Terminal alkynes on reaction with strong base, Sodium hydride (NaH) gives the corresponding…

Q: Show a detailed mechanism for the following reaction. 1. Cl2, NaOH 2. Hзо*

A: Applying concept of haloform reaction followed by acidic hydrolysis.

Q: H2N. Br N° H2N

Q: Show the detailed mechanism for the following reactions. a. он b. H H OCH3 CH;OH H

Q: 20) Provide the mechanism and draw the structure of the major product of the following reaction:…

Q: MeO CH;CH,NH2 CH,OH + O=

A: Given reaction,

Q: (a) Propose a full and reasonable mechanism for the formation of the unusual 5) MAJOR product shown…

A: (a) this question belong to general organic chemistry topic is rearrangement of carbocation and…

Q: Primary alcohols can be dehydrated in an acid-catalyzed reaction. The mechanism is an E2 elimination…

A: Curved Arrow mechanism is shown below for this particular step of E2 elimination reaction.

Q: Predict the major organic product of this reaction and draw the complete mechanism to form it: 1)…

A: This is a organic reaction in which base abstract hydrogen from the alpha position of carbonyl group

Q: Draw the products of the following reaction and show the mechanism; CH3-CH2-CCH3Br-CH3 + CH3OH

A: This is the SN1 reaction .

Q: 5. Provide the product that will result for the following reaction and provide the complete…

A: Diazomethane (CH2N2) is a source of carbene and shows carbene addition across the double bond to…

Q: OH OH a) CH3 b) c) Br

Q: EtO, Eto OMe OMe NH 6 py: ба Ph Ph

A: In this mechanism, lone pair electrons on the N atom is attacked to the carbonyl carbon. Finally HCl…

Q: Show the complete mechanism for the formation of a hemiactetal, when 3-methyl-2-butanone eacts with…

A: Ketone with 1 equivalent of alcohol in acidic medium forms hemiacetal.

Q: The reaction shown below proceeds by both an SN1 and an SN2 mechanism. Draw the products of each…

Q: Provide a detailed mechanism for the following reactions and determine the major product: HO. se +…

A: Note - The given question is a multipart question, hence I solved first three questions according to…

Q: 6. Show the complete mechanism for the following aromatic substitution reaction. Use curved arrows…

A: The complete mechanism of the substitution reaction given below -

Q: When sodium borohydride is added to a mixture of sugar 3 in aqueous basic solution, molecules D and…

A: NaBH4, being a mild reducing agent, reduces the carbonyl group containing compounds (C=O). The…

Q: Predict the main mechanism that occur for the following reaction * CI t-Bu. acetone, 50 C O SN2 E1…

Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

100%

Draw the complete mechanism of the ring opening of the epoxide below with methanol under
both acidic and basic conditions. Based on your mechanisms, explain both the regiochemistry
and stereochemistry observed in the products.
CH,O
CH,OH
cat. HA
CH,OH

Expert Solution

This question has been solved!

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

This is a popular solution!

SEE SOLUTION Check out a sample Q&A here

Step 1

VIEW

Step 2

VIEW

Trending now

This is a popular solution!

Step by step

Solved in 2 steps with 2 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

Predict the product(s) and provide the complete mechanism for each reaction below.
Draw the possible products of this epoxide ring-opening reaction. Use wedge and dash bonds to indicate stereochemistry where appropriate. Ignore any inorganic byproducts. Hll O 1) NaOH / H₂O 2) dilute HCI HIIH Select to Draw
Q, - write a Mechanism that explains hint he stereochemisty (sed pmacal rearangemendy a) CotH6 fonn Hcl b) HeoH O wr,te he Mechanism fer OH CHBrg NAOH (Carbene)
Draw the product of the reaction below including stereochemistry. CH3ONA HI
e Give the mechanism for the following reachou. CHOH exass CHO OCH3 + H-O
The reaction below is a base-catalyzed aldol reaction. O || CH₂-C-H CH3-C-H Ethanal (Acetaldehyde) H I CH3-C-H Ethanal (Acetaldehyde) NaOH Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions AC⇒x= :O: || :CH₂-C-H OH Bl CH3-CH—CH2-CH -CH₂-1-1 a 3-Hydroxybutanal (B-hydroxyaldehyde; formed as a racemic mixture) :0: :0: || CH3—CH—CH2-C-H A tetrahedral carbonyl addition intermediate X
4) Draw the complete electron-pushing arrow mechanism for the following reductions. Explain, using resonance contributors, the regiochemistry that results in each case. ỌMe Na, MeOH ? NH3 CHO Na, MeOH ? NH3
Complete the following reactions by providing the missing product(s). Determine what mechanism operates in each case (SN1, Sn2, E1, or E2), Show the stereochemistry of the product(s) where appropriate. If more than one product us formed circle the major one. Br H,O Br NaOCH;CH;
Please explain and draw the step by step mechanism of oxidation of alkynes with kmno4 and h2o/neutral on an internal alkyne. Please show how the 4 OH was produced and the final product on a clear diagram.
Propose a mechanism for the following reaction (show all curved arrows): Remember the addition of H2O to alkenes.
For each reaction, draw the complete mechanism and the major organic product(s), paying attention to stereochemistry. (a) (b) OH LOH (еxcess) ? ? CH,Cl2 CH2CI2
Consider the following reactants: CI OH Would elimination take place at a significant rate between these reactants? If you said elimination would take place, draw the major products in the upper drawing area. If you said elimination would take place, also draw the complete mechanism for one of the major products in the lower drawing area. If there is more than one major product, you may draw the mechanism that leads to any of them. Oyes Ono