Predict the major products of the following reactions. c. 4−chlorocycloheptene + Hg(OAc) 2 in CH 3 OH d. the product from part (c), treated with NaBH 4

Welcome back, everyone predict the plausible major product or products. Let's begin with the first part of the problem and it says that the starting material is one methyl cyclen one in. So we simply want to draw cyclops, it says cycle pan one in. So we're going to draw a double bond in our five member ring and there's a metal group bonded to carbon number one. So we have our starting L kine and it reacts with mercury to acid it ian methanol. And we have to recall that this reaction is an oxy me cation reaction which follows the Markov Neko rule. What does that mean? Well, essentially it tells us that we must add our L cox C group to the more substituted carbon overall, if we perform deer cation, hydrogen gets bonded to the less substituted carbon. But in this case, we are not yet dealing with deer, we are simply going to add mercury to the less substituted carbon. Now, what does that mean? Well, essentially we are going to take our structure and we're going to introduce our functional groups. First of all, we have our metal group bonded to carbon. Number one, now, the alcoy group, which in this case is the, and now we are going to bond the mercury to the less substituted carbon, it loses one unit of acid. So we have mercury and now we're going to add one unit of acetate. Now, we want to also indicate stereo chemistry. And let's recall that this is NC addition for an NC addition. It essentially means that we are going to add our two substituents in an A NC or trans arrangement relative to the ring. So if we essentially choose to add our coxie group from the top phase of the ring, which essentially means that we have a wedged bond and this leaves us with a dashed bond for the muscle group, then the mercury part will be pointing down on a dash, right? Because they must be pointing in opposite directions relative to the plane of the ring. And also we have our second possibility. What if we add our Coxie group from the bottom face of the ring, then we are going to swap the wedge and the dash so that we will have a dashed bond for the carbon oxygen bond and a wedge or the metal group, which means that the mercury part will be pointing up on a wedged bond. Well, then we have our products. And now for the second part of the problem, we are performing the mercury because it says that the product is treated with sodium boro hydride right. So essentially, if we treat each of our products with sodium bo hydride, we are performing the reduction or basically the deer stuff, which replaces mercury with hydrogen. And notice that we already have one hydrogen at the same carbon where mercury is. Now, what does that mean? Well, we are going to lose a chiral center and if we are going to lose a chiral center, we're going to lose the second chiral center as well. Why? Well, basically because the ring is symmetrical. So we are only going to get one single product with no chiral centers. Let's see what it is. Basically. First of all, we are replacing mercury, mercury with hydrogen and this gives us ch two. So there's no chiral center. And now we can clearly see that there's no more chiral center and the carbon atom that has the alcoy substituent because there are no four different substituents bonded to that carbon based on the symmetry of the ring. So we are going to draw the alcoy part. We have our metox substituent and the methyl group. Those would be our final products. Let's label them for the first part, we have two of them for the second one and we have a one product. Thank you for watching.

Table of contents

Skip topic navigation

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Oxymercuration

Organic Chemistry

10. Addition Reactions

Oxymercuration

Previous problemNext problem

6:10 minutes

Problem 8c,d

Textbook Question

Predict the major products of the following reactions.
c. 4−chlorocycloheptene + Hg(OAc)₂ in CH₃OH
d. the product from part (c), treated with NaBH₄

Verified step by step guidance

Step 1: Analyze the reaction in part (c). The reagent Hg(OAc)₂ in CH₃OH indicates an oxymercuration-demercuration reaction. This reaction typically adds a methoxy group (-OCH₃) to the more substituted carbon of the double bond in a Markovnikov fashion, without rearrangement.

Step 2: Identify the structure of 4-chlorocycloheptene. It is a seven-membered ring with a double bond between carbons 4 and 5, and a chlorine atom attached to carbon 4. The double bond is the reactive site for the oxymercuration reaction.

Step 3: During the oxymercuration step, the double bond reacts with Hg(OAc)₂ in CH₃OH. The mercury acetate (HgOAc) adds to the less substituted carbon of the double bond (carbon 5), while the methoxy group (-OCH₃) adds to the more substituted carbon (carbon 4). This forms an intermediate organomercury compound.

Step 4: In part (d), the product from part (c) is treated with NaBH₄. Sodium borohydride (NaBH₄) is a reducing agent that replaces the mercury group (HgOAc) with a hydrogen atom. This step completes the oxymercuration-demercuration process, yielding the final product.

Step 5: The final product is a 4-chloro-4-methoxycycloheptane. The methoxy group is attached to carbon 4 (the more substituted carbon of the original double bond), and the chlorine atom remains on carbon 4 as it was not involved in the reaction.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Electrophilic Addition

Electrophilic addition is a fundamental reaction mechanism in organic chemistry where an electrophile reacts with a nucleophile, typically involving alkenes or alkynes. In the context of the given reaction, 4-chlorocycloheptene undergoes electrophilic addition with mercuric acetate (Hg(OAc)2), leading to the formation of a more stable carbocation intermediate. This process is crucial for predicting the major products of the reaction.

Markovnikov's Rule

Markovnikov's Rule states that in the addition of HX to an alkene, the hydrogen atom will attach to the carbon with the greater number of hydrogen substituents, while the halide (or other group) will attach to the carbon with fewer hydrogen atoms. This principle helps predict the regioselectivity of the product formed in the reaction of 4-chlorocycloheptene with Hg(OAc)2, guiding the understanding of where the new bonds will form.

Reduction with NaBH4

Sodium borohydride (NaBH4) is a common reducing agent used in organic chemistry to convert carbonyl compounds into alcohols. In the second part of the question, the product from the electrophilic addition reaction is treated with NaBH4, which will reduce any carbonyl groups present, leading to the formation of an alcohol. Understanding this reduction process is essential for predicting the final product of the reaction sequence.

Watch next

Master General properties of oxymercuration-reduction. with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Oxymercuration–reduction, like acid-catalyzed hydration, can be modified to synthesize ethers. Suggest an alkene and the appropriate reaction conditions to synthesize the following ethers.

(b)

Textbook Question

The formation of five-membered ring ethers is an important goal in synthetic organic chemistry because tetrahydrofurans are contained within a number of antitumor natural products. Toward that end, a one-pot synthesis of a bis-THF containing compound was developed (Eur. J. Org. Chem. 2010, 6263–6268). Suggest a mechanism for this transformation.

Textbook Question

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(a)

Textbook Question

Show how you would accomplish the following synthetic conversions.

c. 3-methylpent-1-ene → 3-methylpentan-2-ol

Explain why acid-catalyzed hydration would be a poor choice for the reaction in (c).

Textbook Question

Show how you would accomplish the following synthetic conversions.

a. but-1-ene → 2-methoxybutane

b. 1-iodo-2-methylcyclopentane → 1-methylcyclopentanol

Textbook Question

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]

(b) This reaction sequence was used in the synthesis of (+) -lineatin, a monoterpene aggregation pheromone from the female ambrosia beetle Trypodendron lineatum (Org. Lett. 2004, 6, 1449–1452).

Textbook Question

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]

(c) Oxymercuration–reduction was used in the stereoselective synthesis of the macrolactone core of neopeltolide, a marine macrolide isolated from a Caribbean sponge that has potent anticancer activity (Org. Lett. 2012, 14, 2346–2349).

Multiple Choice

Predict the product of the following reaction.

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap

Predict the major products of the following reactions.c. 4−chlorocycloheptene + Hg(OAc)2 in CH3OHd. the product from part (c), treated with NaBH4

Key Concepts

Electrophilic Addition

Markovnikov's Rule

Reduction with NaBH4

Watch next

Predict the major products of the following reactions.
c. 4−chlorocycloheptene + Hg(OAc)₂ in CH₃OH
d. the product from part (c), treated with NaBH₄