Predict the major product of this series of reactions. The squiggly bond simply indicates the stereochemistry is unknown, i.e., wedge or dash. HBr compound I 1. NaH 2. compound I 3. H2, Lindlar 4. Br2, H20 OH Br Br OH Br Br LOH B. D. C. A.

Organic Chemistry: A Guided Inquiry
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Author:Andrei Straumanis
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Chapter16: Synthesis Workshop 1
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Problem 25E
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### Predicting the Major Product of a Reaction Series

In this exercise, you are given a series of reactions. Your task is to predict the major product. Note that the squiggly bond in the structures indicates that the stereochemistry is unknown (either wedge or dash):

#### Reaction Sequence:
1. **Starting Material:** An alkyne
2. **Reagents and Conditions:**
   1. NaH
   2. Compound I
   3. H₂, Lindlar
   4. Br₂, H₂O

The question is to determine the major product after this sequence of reactions.

#### Multiple Choice Options:
- **A.** 
  ![CHOHBrA](data:image/png;base64,<base64image>)
- **B.** 
  ![CHOHBrB](data:image/png;base64,<base64image>)
- **C.**
  ![CHOHBrC](data:image/png;base64,<base64image>)
- **D.**
  ![CHOHBrD](data:image/png;base64,<base64image>)

The reactions start with an alkyne compound. The initial treatment with HBr leads to the formation of compound I. This is followed by the addition of NaH, then compound I, hydrogenation with Lindlar's catalyst to form a cis-alkene, and finally the bromination in the presence of water.

#### Explanation:
1. **HBr Addition:** 
   - The alkyne reacts with HBr to form a bromo-alkene (Compound I).

2. **NaH and Compound I Reaction:**
   - This step is a bit ambiguous without the structure of Compound I, but likely involves some sort of substitution.

3. **Partial Hydrogenation:**
   - Lindlar's catalyst converts the alkyne (or substituted alkyne) into a cis-alkene.

4. **Bromination:**
   - The final step involving Br₂ in water adds a bromine and a hydroxyl group (anti-addition) to the cis-alkene, resulting in a bromohydrin.

Based on the reaction sequence and mechanisms, the main product will have a bromo and a hydroxyl group on the previously double-bonded carbon atoms.

Examining the given options:
- **Option A** and **Option B** are the most likely candidates because they follow the bromohydrin formation
Transcribed Image Text:### Predicting the Major Product of a Reaction Series In this exercise, you are given a series of reactions. Your task is to predict the major product. Note that the squiggly bond in the structures indicates that the stereochemistry is unknown (either wedge or dash): #### Reaction Sequence: 1. **Starting Material:** An alkyne 2. **Reagents and Conditions:** 1. NaH 2. Compound I 3. H₂, Lindlar 4. Br₂, H₂O The question is to determine the major product after this sequence of reactions. #### Multiple Choice Options: - **A.** ![CHOHBrA](data:image/png;base64,<base64image>) - **B.** ![CHOHBrB](data:image/png;base64,<base64image>) - **C.** ![CHOHBrC](data:image/png;base64,<base64image>) - **D.** ![CHOHBrD](data:image/png;base64,<base64image>) The reactions start with an alkyne compound. The initial treatment with HBr leads to the formation of compound I. This is followed by the addition of NaH, then compound I, hydrogenation with Lindlar's catalyst to form a cis-alkene, and finally the bromination in the presence of water. #### Explanation: 1. **HBr Addition:** - The alkyne reacts with HBr to form a bromo-alkene (Compound I). 2. **NaH and Compound I Reaction:** - This step is a bit ambiguous without the structure of Compound I, but likely involves some sort of substitution. 3. **Partial Hydrogenation:** - Lindlar's catalyst converts the alkyne (or substituted alkyne) into a cis-alkene. 4. **Bromination:** - The final step involving Br₂ in water adds a bromine and a hydroxyl group (anti-addition) to the cis-alkene, resulting in a bromohydrin. Based on the reaction sequence and mechanisms, the main product will have a bromo and a hydroxyl group on the previously double-bonded carbon atoms. Examining the given options: - **Option A** and **Option B** are the most likely candidates because they follow the bromohydrin formation
**Title: Identifying the Reaction that Produces a Stereocenter**

**Question:**
Which reaction will produce a stereocenter?

**Options:**
A. 
Alkene structure (2-butene) undergoing a reaction with \( Br_2 \). 

B. 
Alkene structure (2-butene) undergoing hydrogenation with \( H_2 \) in the presence of Pt (platinum catalyst).

C. 
Alkene structure (2-methyl-2-butene) undergoing hydroboration-oxidation:
   1. \( BH_3 \), THF 
   2. \( H_2O_2 \), \( OH^- \).

D. Two of the above

E. None of the above

**Explanation of Graph/Diagram:**

The image displays the following three reactions for an alkene compound:

Option A: This shows an alkene reacting with bromine (\( Br_2 \)). This typically leads to the anti-addition of bromine across the double bond, which can create a stereocenter if the substrate allows for it.

Option B: This represents the hydrogenation of an alkene using hydrogen (\( H_2 \)) and a platinum (Pt) catalyst. This reaction usually results in the syn-addition of hydrogen atoms across the double bond.

Option C: This depicts the hydroboration-oxidation of an alkene, which is a two-step process. In the first step, the alkene reacts with borane (\( BH_3 \)) in tetrahydrofuran (THF) to form an organoborane intermediate. In the second step, the organoborane is oxidized by hydrogen peroxide (\( H_2O_2 \)) in an alkaline solution (\( OH^- \)) to form the alcohol via anti-Markovnikov addition.

Please analyze these reactions to determine which one produces a stereocenter. A stereocenter (or chiral center) is an atom in a molecule that is attached to four different groups, leading to non-superimposable mirror images or stereoisomers.
Transcribed Image Text:**Title: Identifying the Reaction that Produces a Stereocenter** **Question:** Which reaction will produce a stereocenter? **Options:** A. Alkene structure (2-butene) undergoing a reaction with \( Br_2 \). B. Alkene structure (2-butene) undergoing hydrogenation with \( H_2 \) in the presence of Pt (platinum catalyst). C. Alkene structure (2-methyl-2-butene) undergoing hydroboration-oxidation: 1. \( BH_3 \), THF 2. \( H_2O_2 \), \( OH^- \). D. Two of the above E. None of the above **Explanation of Graph/Diagram:** The image displays the following three reactions for an alkene compound: Option A: This shows an alkene reacting with bromine (\( Br_2 \)). This typically leads to the anti-addition of bromine across the double bond, which can create a stereocenter if the substrate allows for it. Option B: This represents the hydrogenation of an alkene using hydrogen (\( H_2 \)) and a platinum (Pt) catalyst. This reaction usually results in the syn-addition of hydrogen atoms across the double bond. Option C: This depicts the hydroboration-oxidation of an alkene, which is a two-step process. In the first step, the alkene reacts with borane (\( BH_3 \)) in tetrahydrofuran (THF) to form an organoborane intermediate. In the second step, the organoborane is oxidized by hydrogen peroxide (\( H_2O_2 \)) in an alkaline solution (\( OH^- \)) to form the alcohol via anti-Markovnikov addition. Please analyze these reactions to determine which one produces a stereocenter. A stereocenter (or chiral center) is an atom in a molecule that is attached to four different groups, leading to non-superimposable mirror images or stereoisomers.
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