Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 30: Problem 701

Cadinene, \(\mathrm{C}_{15} \mathrm{H}_{24}\), is a sesquiterpene occurring in the essential oils of junipers and cedars. Dehydrogenation gives the naphthalene hydrocarbon cadalene. (a) What is the IUPAC name for cadalene. (b) Give a rational synthesis of cadalene from toluene and any necessary aliphatic compounds.

Short Answer

Expert verified
(a) The IUPAC name for cadalene is 1,6-dimethyl-4-(propan-2-yl)naphthalene. (b) The synthesis of cadalene from toluene involves alkylation and dehydrogenation steps utilizing isopropyl chloride, 1-chloropropane, AlCl3, and Pd/C as catalysts.

Step by step solution

01

Identify the Structure of Cadalene

Cadalene is formed by the dehydrogenation of cadinene, C15H24. The structure of cadalene is a naphthalene hydrocarbon. Based on this information, we can deduce the structure of cadalene as follows: ![Cadalene Structure](https://upload.wikimedia.org/wikipedia/commons/thumb/6/60/Cadalene.svg/1200px-Cadalene.svg.png)
02

Find the IUPAC Name for Cadalene

The IUPAC name for this compound is based on the longest continuous carbon chain and the presence of functional groups. In this case, the parent chain is naphthalene, and there are no functional groups present. Thus, cadalene's IUPAC name is: 1,6-dimethyl-4-(propan-2-yl)naphthalene (a) The IUPAC name for cadalene is 1,6-dimethyl-4-(propan-2-yl)naphthalene.
03

Synthesize Cadalene from Toluene and Aliphatic Compounds

A rational synthesis of cadalene from toluene involves the following steps: 1. Friedel-Crafts Alkylation of toluene with isopropyl chloride (using AlCl3 as a catalyst) to form 1-isopropyl-4-methylbenzene. \( \text{Toluene + Isopropyl chloride} \overset{\text{AlCl}_3}{\longrightarrow} \text{1-isopropyl-4-methylbenzene}\) 2. Dehydrogenation of 1-isopropyl-4-methylbenzene using palladium/carbon (Pd/C) as a catalyst to form 1-isopropyl-4-methylnaphthalene. \( \text{1-isopropyl-4-methylbenzene} \overset{\text{Pd/C}}{\longrightarrow} \text{1-isopropyl-4-methylnaphthalene}\) 3. Friedel-Crafts Alkylation of 1-isopropyl-4-methylnaphthalene with 1-chloropropane (using AlCl3 as a catalyst) to form 1-isopropyl-4-methyl-6-propylnaphthalene. \( \text{1-isopropyl-4-methylnaphthalene + 1-chloropropane} \overset{\text{AlCl}_3}{\longrightarrow} \text{1-isopropyl-4-methyl-6-propylnaphthalene }\) 4. Dehydrogenation of 1-isopropyl-4-methyl-6-propylnaphthalene using palladium/carbon (Pd/C) as a catalyst to form cadalene. \( \text{1-isopropyl-4-methyl-6-propylnaphthalene} \overset{\text{Pd/C}}{\longrightarrow} \text{Cadalene }\) (b) The synthesis of cadalene from toluene involves alkylation and dehydrogenation steps utilizing isopropyl chloride, 1-chloropropane, AlCl3, and Pd/C as catalysts.

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

In 1904, Franz Knoop outlined a scheme for the biological oxidation of fatty acids that was shown \(-50\) years later \(-\) to be correct. In his key experiments, he fed rabbits fatty acids of formula \(\mathrm{C}_{6} \mathrm{H}_{5}\left(\mathrm{CH}_{2}\right)_{\mathrm{n}}\) COOH. When the side chain \((\mathrm{n}+1)\) contained an even number of carbons, a derivative of phenylacetic acid, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{COOH}\), was excreted in the urine; an odd number, and a derivative of benzoic acid was excreted. What general hypothesis can you formulate from these results?

A compound named Y-terpinene, an isomer of \(\alpha\) -terpinene, is isolated along with the a isomer from the oils of a number of plant products. Upon ozonolysis, followed by an oxidative workup, \(\Upsilon\) -terpinene yields two compounds, one of which is 4 -methyl-3-oxopentanoic acid. The second compound is an acid which decarboxylates upon heating and gives acetone. Two structures consistent with the data are possible for \(\Upsilon\) -terpinene. What are they? On the basis of the isoprene rule, one of them can be discarded as highly improbable. What is the structure of \(\Upsilon\) -terpinene?

Which of the following compounds would exhibit detergent properties? (a) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{~N}^{+}\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Cl}^{-}\) (b) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{COOCH}_{3}\) (c) \(\mathrm{CH}_{3}\left(\mathrm{CH}_{2}\right)_{10} \mathrm{CH}_{2} \mathrm{SO}^{-}{ }_{3} \mathrm{Na}^{+}\)

Spermaceti (a wax from the head of the sperm whale) resembles high-molecular weight hydrocarbons in physical properties and inertness toward \(\mathrm{Br}_{2} / \mathrm{CCl}_{4}\) and \(\mathrm{KMnO}_{4} ;\) on qualitative analysis it gives positive tests only for carbon and hydrogen. However, its infrared spectrum shows the presence of an ester group, and quantitative analysis gives the empirical formula \(\mathrm{C}_{16} \mathrm{H}_{32} \mathrm{O}\) A solution of the wax and \(\mathrm{KOH}\) in ethanol is refluxed for a long time. Titration of an aliquot shows that one equivalent of base has been consumed for every \(475 \pm 10\) grams of wax. Water and ether are added to the cooled reaction mixture, and the aqueous and ethereal layers are separated. Acidification of the aqueous layer yields a solid \(\mathrm{A}\), m.p. \(62-3^{\circ}\), neutralization equivalent \(260 \pm 5\). Evaporation of the ether layer yields a solid B, m.p. \(48-9^{\circ}\). Reduction by LiAlHi \(_{4}\) of either spermaceti or A gives \(B\) as the only product. B is normal alcohol. What is the structure of spermaceti?

Carbon dioxide is required for the conversion of acetyl CoA into fatty acids. Yet when carbon dioxide labeled with \({ }^{14} \mathrm{C}\) is used, none of the labeled carbon appears in the fatty acids that are formed. How do you account for these facts?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Chemistry Branches

Read Explanation

Kinetics

Read Explanation

Physical Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Organic Chemistry

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