Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 24: Problem 612

How many and what kind of stereoisomers would you expect for each of the following compounds: (a) methylethyl-s-butylsulfonium bromide (b) \(\left[\mathrm{CH}_{3}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{~S}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\right]^{2(+)} 2 \mathrm{Br}^{-}\)

Short Answer

Expert verified
For methylethyl-s-butylsulfonium bromide (compound A), there are 2 stereoisomers, and for $\left[\mathrm{CH}_{3}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{~S}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\right]^{2(+)} 2 \mathrm{Br}^{-}$ (compound B), there are 4 stereoisomers.

Step by step solution

01

Compound A: Methylethyl-s-butylsulfonium bromide

Step 1: Identify Chiral Centers For methylethyl-s-butylsulfonium bromide, since it is an onium ion, the carbon atoms are not chiral centers. The sulfonium ion contains the most relevant chiral center. Step 2: Calculate Number of Stereoisomers Since there is only 1 chiral center in compound A, we can use the formula \(2^n\) to calculate the number of stereoisomers: \(2^1 = 2\) There are 2 stereoisomers for compound A.
02

Compound B: $\left[\mathrm{CH}_{3}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{~S}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\right]^{2(+)} 2 \mathrm{Br}^{-}$

Step 1: Identify Chiral Centers For compound B, the entire molecule should be considered. The two chiral centers in this molecule are the two carbon atoms bonded to the sulfur atoms. Step 2: Calculate Number of Stereoisomers Since there are 2 chiral centers in compound B, we can use the formula \(2^n\) to calculate the number of stereoisomers: \(2^2 = 4\) There are 4 stereoisomers for compound B.
03

Conclusion

In summary, we can expect 2 stereoisomers for methylethyl-s-butylsulfonium bromide (compound A) and 4 stereoisomers for $\left[\mathrm{CH}_{3}\left(\mathrm{C}_{2} \mathrm{H}_{5}\right) \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{~S}\left(\mathrm{CH}_{3}\right) \mathrm{C}_{2} \mathrm{H}_{5}\right]^{2(+)} 2 \mathrm{Br}^{-}$ (compound B).

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Give each of the following pairs of compounds a chemical test, preferably a test-tube reaction, which would serve to distinguish one from the other. (a) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SH}\) and \(\mathrm{CH}_{3} \mathrm{SCH}_{3}\) (b) \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{~S}\right)_{2}\) and \(\left(\mathrm{CH}_{3} \mathrm{CH}_{2}\right)_{2} \mathrm{~S}\) (c) \(\mathrm{CH}_{3} \mathrm{~S}(\mathrm{O}) \mathrm{OCH}_{3}\) and \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SO}_{3} \mathrm{H}\) (d) \(\mathrm{CH}_{3} \mathrm{~S}(\mathrm{O}) \mathrm{OCH}_{3}\) and \(\mathrm{CH}_{3} \mathrm{~S}(\mathrm{O})_{2} \mathrm{CH}_{3}\) (e) \(\mathrm{CH}_{3} \mathrm{SCH}_{2} \mathrm{CH}_{2} \mathrm{OH}\) and \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{SH}\)

Show how you would synthesize the following compounds from the indicated starting materials and any desired inorganic reagents. (a) di-n-octyl sodium sulfosuccinate, \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{7} \mathrm{O}_{2} \mathrm{CCH}_{2} \mathrm{CH}\left(\mathrm{SO}_{3} \mathrm{Na}\right)-\mathrm{CO}_{2} \cdot\left(\mathrm{CH}_{2}\right)_{7} \mathrm{CH}_{3}\) ("Aerosol" detergent) from maleic anhydride and n-octyl alcohol. (b) \(\left(\mathrm{CH}_{2}\right)_{3}\left(\mathrm{SO}_{3} \mathrm{H}\right)_{2}\) from \(\left(\mathrm{CH}_{2}\right)_{3} \mathrm{Br}_{2}\) (c) methyl 1 -butanesulfinate from \(\mathrm{n}\) -butyl bromide (a) from C=Cc1ccccc1 (e) optically active ethyl benzenesulfinate from optically active 2-octyl- benzenesulfinate.

(a) Methyl chloromethyl sulfone reacts with strong alkali to yield ethylene and sodium sulfite. Write a mechanism for this reaction which is in accord with the reagents and the products. (b) Butadiene when heated with sulfur dioxide undergoes 1,4 -addition with formation of an unsaturated cyclic sulfone. How might this sulfone (in conjunction with the reaction which gives an alkene from an a-halosulfone) be used in a synthesis of cyclobutadiene?

The sulfhydryl group of coenzyme A plays an important role in the biosynthesis of fatty acids from units of acetic acid. The key steps are suggested to be carboxylation with carbon dioxide of acetyl coenzyme \(\mathrm{A}\) (which is a thioester abbreviated as O=CSC(=O)O to give malonyl coenzyme \(\mathrm{A}\) followed by condensation of the malonyl coenzyme A with acetyl coenzyme \(\mathrm{A}\), or a molecule of an acyl coenzyme \(\mathrm{A}\), to produce an acyl malonyl coenzyme \(\mathrm{A}\) This is followed by decarboxylation and reduction to an acyl coenzyme \(A\) with two more carbon atoms than the starting acyl coenzyme \(\mathrm{A}\). Each repetition of the process gives a fatty acid (or thioester of a fatty acid) with an additional two carbons. All the steps are of course controlled by specific enzymes. \(5^{\prime}-\) (adenosine 3' -phosphate) \(-\mathrm{OP}(\mathrm{O})(\mathrm{OH}) \mathrm{OP}(\mathrm{O})(\mathrm{OH}) \mathrm{OCH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\) \(\mathrm{CH}(\mathrm{OH})-\mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{CONH}\left(\mathrm{CH}_{2}\right)_{2} \mathrm{SH}\) coenzyme \(\mathrm{A}(\mathrm{CoA}\) SH ) (a) Write out the complete structure of coenzyme A as corresponds to the above condensed formula; what products would you expect coenzyme \(\mathrm{A}\) to give on vigorous hydrolysis? (b) Work out the steps for synthesis of hexanoic acid from acetic acid with the acid of coenzyme \(A\), using the abbreviation CoA-SH and indicating the general nature of each step in terms of the kind of reagents that might be used to achieve it in ordinary laboratory operations. What advantages would you expect to accrue from CoA-SH as compared to CoA-OH as the acyl carrier? (c) Suppose the enzymic synthesis of hexanoic acid to be carried on in the presence of radioactive carbon dioxide; would the postulated course of the reaction be precluded if the hexanoic acid produced were completely devoid of radioactivity? Explain in detail.

Mustard gas or bis-( \(\beta\) -chloroethyl) sulfide, \(\left(\mathrm{C} 1 \mathrm{CH}_{2} \mathrm{CH}_{2}\right)_{2} \mathrm{~S}\), is an oily liquid that was used extensively as poison gas in World War I. It is a deadly vesicant that causes blindness and numerous other effects. The active agent is actually the cyclic sulfonium salt which reacts with nucleophilic materials in the body. The formation of the cyclic sulfonium salt can be regarded as an internal or intramolecular \(\mathrm{S}_{\mathrm{N}} 2\) displacement reaction. Write out this reaction mechanism. What mechanism does this process suggest for the subsequent reaction of the cyclic sulfonium salt with nucleophilic reagents?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Chemical Reactions

Read Explanation

Organic Chemistry

Read Explanation

Kinetics

Read Explanation

Inorganic Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.

Sign-up for free