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Chapter 14: Q 55P (page 750)

In 2012, a group led by Professor Masayuki Satake of the University of Tokyo reported the isolation and structure determination of a toxin from a marine algal bloom that decimated the fish population off the New Zealand coast in 1998. Extensive mass spectrometry and NMR experiments ultimately led to the structure shown below, named Brevisulcenal-F. (See Journal of the American Chemical Society, 2012, 134, 4963-4968.) This structure holds the record for the largest number of fused rings, at 17.

Brevisulcenal-F

a. How many ether groups are present?

b. How many alcohol groups are present? Classify the alcohols as 1o or 2o or 3o.

c. Are there any other oxygen-containing functional groups? Which, if any?

Short Answer

Expert verified

a) 24 ether groups are present.

b) There are thirteen secondary alcohols and no primary or tertiary alcohol.

c) There is one aldehyde present as oxygen-containing functional group.

Step by step solution

01

Explanation of part (a) and part (b):

The ether groups are marked as large dots and alcohols are indicated as OH in the structure. The ether count is 24 and there are thirteen secondary alcohols present in the structure with no primary or tertiary alcohol.

Ether and alcohol groups present in Brevisulcenal-F

02

Explanation of part (c):

There is one aldehydic group which is present as oxygen-containing functional group in the structure. This structure contains 17 fused rings and 7 other rings and is made by an algae.

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Most popular questions from this chapter

Question: Both LiAlH4and Grignard reagents react with carbonyl compounds to give alkoxide ion intermediates (that become protonated in an aqueous workup). Those alkoxides can react with 1o or methyl alkyl halides or tosylates to give ethers. Show how the following ethers can be formed in this two -step process. As starting materials, you may use any reactants containing 8carbons or fewer.

Write structural formulas for the following compounds

  1. methyl isopropyl ether (b) di-iso-butyl ether (c) 2-methoxyoctane

(d) diallyl ether (e) allyl ethyl ether (f) cycloheptane oxide

(g) trans-2,3-epoxyheptane (h) (2R,3S)-2-ethoxypentan-3-ol (i) cis-2,3-dimethyloxirane

Question: (a) Predict the values of m/zand the structures of the most abundant fragments you would observe in the mass spectrum of di-n-propyl-ether.

(b) Give logical fragmentations to account for the following ions observed in the mass spectrum of 2-methoxypentane: 102,87,71,59,31.

Question. The 2001 Nobel Prize in Chemistry was awarded to three organic chemists who have developed methods for catalytic asymmetric synthesis. An asymmetric (or enantioselective) synthesis is one that converts an achiral starting material into mostly one enantiomer of a chiral product. K. Barry Sharpless (The Scripps Research Institute) developed an asymmetric epoxidation of allylic alcohols that gives excellent chemical yields and greater than 90% enantiomeric excess.

The Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartarate ester as the reagents. The following epoxidation of geraniol is typical.

  1. Which of these reagents is most likely to be the actual oxidizing agent? That is, which reagent is reduced in the reaction? What is the likely function of the other reagents?
  2. When achiral reagents react to give a chiral product, that product is normally formed as a racemic mixture of enantiomers. How can the Sharpless epoxidation give just one nearly pure enantiomer of the product?
  3. Draw the other enantiomer of the product. What reagents would you use if you wanted to epoxidize geraniol to give this other enantiomer?

Question. Propose a mechanism for the following reaction.
See all solutions

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