1. Predict the major products of the following reactions. Include stereochemistry where appeopriate a. b. d. e. c. £. OH stou -OH OH OH OTS + X-moto- H₂C wwwOH + + HI OH HBr NaCN/DMSO OH + HCI OH F3C- sofa sofa. SOCI₂ PBry CH₂S N DMSO
1. Predict the major products of the following reactions. Include stereochemistry where appeopriate a. b. d. e. c. £. OH stou -OH OH OH OTS + X-moto- H₂C wwwOH + + HI OH HBr NaCN/DMSO OH + HCI OH F3C- sofa sofa. SOCI₂ PBry CH₂S N DMSO
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...
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**Topic: Predicting Major Products of Chemical Reactions**
**Objective:** Analyze the given reactions and determine the major products, considering stereochemistry where relevant.
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1. **Reaction Descriptions**
**a.** Reaction involves a primary alcohol reacting with HBr (hydrobromic acid).
**b.** Reaction involves a cyclic alcohol reacting with HI (hydroiodic acid).
**c.** Reaction involves a secondary alcohol reacting with HCl (hydrochloric acid).
**d.** A secondary alcohol reacts with a benzoyl chloride derivative.
**e.** Two reactions:
- A tosylate group (\(OTS\)) substituted alkane reacting with sodium cyanide (NaCN) in dimethyl sulfoxide (DMSO).
- A secondary alcohol with trifluoromethanesulfonyl chloride, leading to a product formed in the presence of sodium methyl sulfinate in DMSO.
**f.** Reaction involves a secondary alcohol reacting with thionyl chloride (SOCl₂).
**g.** A cyclic alcohol reacting with phosphorus tribromide (PBr₃).
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2. **Analysis of Reactions**
- **Reactions a, b, c:** Typically proceed via nucleophilic substitution (SN1 or SN2), potentially generating alkyl halides.
- **Reaction d:** Likely involves esterification or acylation, forming an ester linkage.
- **Reaction e (first):** Substitution reaction converting the tosyl group to a nitrile.
- **Reaction e (second):** Involves conversion to a sulfonate ester, which may further undergo elimination or substitution.
- **Reaction f:** Conversion to an alkyl chloride, possibly with retention or inversion of stereochemistry depending on the conditions.
- **Reaction g:** Results in the formation of an alkyl bromide from an alcohol.
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Each reaction requires consideration of the mechanism and the influence of stereochemistry on the major product.
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