### Reaction Products Prediction#### Objective:Predict the products for each of the following reactions involving allylic alcohols and titanium-based catalysts with diethyl tartrate.#### Reactions:1. **Reaction (a)** - **Reactants:** - Cyclohexen-1-ylmethanol - Reagents: Ti(OCH(CH_3)_2)_4, (+)-DET, t-Butyl hydroperoxide - **Expected Product:** To be predicted2. **Reaction (b)** - **Reactants:** - 3-penten-2-ol (an allylic alcohol) - Reagents: Ti(OCH(CH_3)_2)_4, (-)-DET, t-Butyl hydroperoxide - **Expected Product:** To be predicted3. **Reaction (c)** - **Reactants:** - Prop-2-en-1-ol (an allylic alcohol) - Reagents: Ti(OCH(CH_3)_2)_4, (+)-DET, t-Butyl hydroperoxide - **Expected Product:** To be predicted4. **Reaction (d)** - **Reactants:** - 3-buten-2-ol (an allylic alcohol) - Reagents: Ti(OCH(CH_3)_2)_4, (-)-DET, t-Butyl hydroperoxide - **Expected Product:** To be predicted#### Explanation:These reactions involve the Sharpless asymmetric epoxidation, where an allylic alcohol is converted into an epoxide. The stereoselectivity of the reaction is guided by the chirality of diethyl tartrate (DET). The orientation of the epoxide in the product depends on whether (+)-DET or (-)-DET is used.- (+)-DET typically favors the formation of the epoxide on one face of the double bond.- (-)-DET usually favors the formation of the epoxide on the opposite face.#### Notes:- **Ti(OCH(CH_3)_2)_4:** Titanium isopropoxide, a catalyst in the reaction- **DET:** Diethyl tartrate, provides chiral environment- **t-Butyl Hydroperoxide:** An oxidizing agentBy identifying the specific stereochemical outcome for each starting material and reagent combination, one can predict the precise 3D orientation of the resultant

IntroductionWe might point out that one of the core concepts of organic chemistry is the prediction…

14.16 Predict the products for each of the following reactions: (a) (c) -OH OH to -0-0-H TOCH(CH3)214 (+)-DET -0-0-H Ti[OCH(CH3)214 (+)-DET ? ? (b) (d) OH -OH -0-0-H T[OCH(CH3)214 (-)-DET -0-0-H Ti[OCH(CH3)214 (-)-DET ?

14.16 Predict the products for each of the following reactions: (a) (c) -OH OH to -0-0-H TOCH(CH3)214 (+)-DET -0-0-H Ti[OCH(CH3)214 (+)-DET ? ? (b) (d) OH -OH -0-0-H T[OCH(CH3)214 (-)-DET -0-0-H Ti[OCH(CH3)214 (-)-DET ?

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: List the cobalt complexes in order of increasing Kstab values. Using one of the cobalt(II) complexes…

A: We can compare the stability of coordination complexes with same metal ion in same oxidation state…

Q: Question 7 Page 5 of 6 State the effect on the rate (increase, decrease or stay the same) of…

A: According to Q&A guidelines of Bartleby, we are supposed to answer only the first 3 sub-parts of…

Q: Consider a reaction between: Fe(C2H3O2)2 and Na2CO3. Choose the appropriate products: A:FeCO3(s)…

Q: Calculate the solubility of PLCCNy IN a 12M solution of CacCN), KSP FOR Pb (CN) = 4.8x10-51

Q: (a) Put in order of increasing rate of substitution by NH3 in the following complexes (a)…

Q: Match the reaction to their product. Fe(NO3)3 + NH4OH White precipitate Fe(NO3)3 + KSCN Red colour…

Q: An unknown solution is analyzed by selective precipitation. The solution is treated with 6M HCl,…

A: The cation precipitate with HCl and is soluble in hot water, gives yellow color with sodium…

Q: Which of the reactions below will produce this compound? A. (a) B. (b) C. Either D. Neither (a) (b)…

A: The epoxide ring opening of option a with strong nucleophile sodium bromide proceeds through the SN2…

Q: MgBr (a) (ii) H,O* (b) (i) Li, ether -Br H3C' (ii) H,0* (c) (i) 2 EtMgBr (ii) H,O* (d) PhB(OH)2,…

A: Product of the above reaction depends on the reagent used . The reaction and mechanism occurs on the…

Q: Please and the detall step by step a) b) Br 1) Mg, Et₂O 2) CO2(s), puis H3O+ 12, KI, KOH excès puis…

A: Given are organic reactions.Let's see products in next step.

Q: (b) Х + NH; —Y

A: Trans Effect is defined as the tendency of a particular group to direct the incoming group to occupy…

Q: [2] For the following pair of compounds, identify the most thermodynamically stable complex…

A: The compound containing chelate ring is more stable than non chelating compound. In the 2nd complex…

Q: theoretical yield

A: Number of moles = mass/molar mass Mass /theoritical yield = moles x molar mass

Q: What is the concentration of free Hg2+ in 2.6061e-4 M Hg(NO3)2 and 1.1005 M NH3? Hg2+ + 4 NH3 →…

A: Formation constant or binding constant is defined as the equilibrium constant for the formation of a…

Q: Use the data given here to calculate the values of AG at 25 °C for the reaction described by the…

A: The given reaction is : A + B ⇌ C In this question, it has been found to calculate the ∆G°f at…

Q: Predict the nature, including the correct special isomerisation (i.e. cis/trans) when necessary, of…

A: A question based on trans effect, which is to be accomplished.

Q: IOTO 11. Which of the following coordination compounds is colof 3+ 3+ (C) [Ag(NH3)2]* (D) [Ti(H;O)6]…

Concept explainers

Catalysis and Enzymatic Reactions

Catalysis is the kind of chemical reaction in which the rate (speed) of a reaction is enhanced by the catalyst which is not consumed during the process of reaction and afterward it is removed when the catalyst is not used to make up the impurity in the product. The enzymatic reaction is the reaction that is catalyzed via enzymes.

Lock And Key Model

The lock-and-key model is used to describe the catalytic enzyme activity, based on the interaction between enzyme and substrate. This model considers the lock as an enzyme and the key as a substrate to explain this model. The concept of how a unique distinct key only can have the access to open a particular lock resembles how the specific substrate can only fit into the particular active site of the enzyme. This is significant in understanding the intermolecular interaction between proteins and plays a vital role in drug interaction.

Question

### Reaction Products Prediction

#### Objective:
Predict the products for each of the following reactions involving allylic alcohols and titanium-based catalysts with diethyl tartrate.

#### Reactions:

1. **Reaction (a)**
- **Reactants:**
- Cyclohexen-1-ylmethanol
- Reagents: Ti(OCH(CH_3)_2)_4, (+)-DET, t-Butyl hydroperoxide
- **Expected Product:** To be predicted

2. **Reaction (b)**
- **Reactants:**
- 3-penten-2-ol (an allylic alcohol)
- Reagents: Ti(OCH(CH_3)_2)_4, (-)-DET, t-Butyl hydroperoxide
- **Expected Product:** To be predicted

3. **Reaction (c)**
- **Reactants:**
- Prop-2-en-1-ol (an allylic alcohol)
- Reagents: Ti(OCH(CH_3)_2)_4, (+)-DET, t-Butyl hydroperoxide
- **Expected Product:** To be predicted

4. **Reaction (d)**
- **Reactants:**
- 3-buten-2-ol (an allylic alcohol)
- Reagents: Ti(OCH(CH_3)_2)_4, (-)-DET, t-Butyl hydroperoxide
- **Expected Product:** To be predicted

#### Explanation:
These reactions involve the Sharpless asymmetric epoxidation, where an allylic alcohol is converted into an epoxide. The stereoselectivity of the reaction is guided by the chirality of diethyl tartrate (DET). The orientation of the epoxide in the product depends on whether (+)-DET or (-)-DET is used.

- (+)-DET typically favors the formation of the epoxide on one face of the double bond.
- (-)-DET usually favors the formation of the epoxide on the opposite face.

#### Notes:
- **Ti(OCH(CH_3)_2)_4:** Titanium isopropoxide, a catalyst in the reaction
- **DET:** Diethyl tartrate, provides chiral environment
- **t-Butyl Hydroperoxide:** An oxidizing agent

By identifying the specific stereochemical outcome for each starting material and reagent combination, one can predict the precise 3D orientation of the resultant

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: Introduction

VIEW

Step 2: solution

VIEW

Solution

VIEW

Step by step

Solved in 3 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

What is the concentration of free Hg2+ in 2.6061e-4 M Hg(NO3)2 and 1.1005 M NH3? Hg2+ + 4 NH3 → [Hg(NH3)4]2+ Kf = 1.800e+19
Kk.301.
Kk.266.
4. A solution at pH 7.0 contains Cu²+ and NH3. (a) What is the ratio (CuOH*)/(Cu²+)? (b) What is the ratio (NH)/(NH₂)? (c) Are there any hydroxo-complexes of Cu present at concentrations greater than that of CuOH+?
3. a. (i) Starting from K₂[PtC14], plan synthetic routes to the two complexes A and B shown below, using your knowledge of the trans effect. Formulate each step by drawing structures of each complex and give a full explanation for your choices. Make sure to assign the correct charges to each complex in each case. 7- 7- (ii) NCS NH₂ -Pt-Br CI NO₂ CI-Pt-OH CO B Write a detailed discussion of the two factors that may contribute to the overall trans-directing ability of a particular ligand, considering thermodynamic and kinetic aspects. Use appropriate examples and orbital sketches to support your explanations.
Kk.38.
At pH 1, superoxide ions are is largely present in water as? О НО2 O H202" O HO22- O 02 O H2022+ QUESTION 2 Au(1) complexes are aurophilic and isoelectronic with O Hg(II) O Pt(II) O Pd(1) O Ir(III) O Rh(I)
Acetic acid, CH3COOH, is contained in vinegar. Suppose acetic acid was formed from its elements, according to the following equation: 2C(graphite) + 2H2(g) + O2(g) à CH3COOH(l) Find the enthalpy change, ∆H , for this reaction, using the following data: CH3COOH(l) + 2O2(g) à 2CO2(g) + 2H2O(l)∆H= -871 kJ C(graphite) + O2(g) àCO2(g)∆H = -394 kJ H2(g) + ½ O2(g) à H2O(l)∆H = -286 kJ