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Chapter 17: Q17-58E (page 567)

Benzoquinone is an excellent dienophile in the Diels – Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3 butadiene? From reaction with 2 equivalents of 1,3 butadiene?

Short Answer

Expert verified

The answer is

From 1 equivalent of butadiene,

From 2 equivalent of butadiene,

Step by step solution

01

Diels Alder reaction

The Diels Alder reaction is a [4+2] cycloaddition reaction. It takes place in the presence of heat. A diene and a dienophile undergo electron rearrangement in this reaction to give a cyclic product.

02

Explanation

From 1 equivalent of butadiene

Formation of 4a,5,8,8a-tetrahydronaphthalene-1,4-dione

In this, 3 double bonds in reactants are converted to 1 double bond and 2 single bonds in the product.

From 2 equivalent of butadiene,

Formation of 1,4,4a,5,8,8a,9a,10a-octahydroanthracene-9,10-dione

In this, 6 double bonds in reactants are converted to 2 double bond and 4 single bonds in the product.

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Most popular questions from this chapter

The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:

(a) tert-butyldimethylsilyl chloride (TBS-Cl)

(b) triisopropylsilyl chloride (TIPS-Cl)

(c) triethylsilyl chloride (TES-Cl)

Name and assign R or S stereochemistry to the product (s) you would obtain by reaction of the following substance with ethylmagnesium bromide. Is the product chiral? Is it optically active? Explain.

The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.

A compound of unknown structure gave the following spectroscopic data:

Mass spectrum:M+=88.1

IR: 3600 cm-1

1HNMR: 1.4δ (2H, quartet, J=7Hz); 1.2δ (6H, singlet); 1.0δ (1H, singlet); 0.9δ (3H, triplet, J=7Hz)

13CNMR: 74, 35, 27, 25δ

(a) Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.

(b) How many protons (H) does the compound contain?

(c) What functional group(s) does the compound contain?

(d) How many carbons does the compound contain?

(e) What is the molecular formula of the compound?

(f) What is the structure of the compound?

(g) Assign peaks in the molecule’s NMR spectrum corresponding to specific protons.

What carbonyl compounds might you start with to prepare the following compounds by Grignard reaction? List all possibilities.

(a) 2-Methyl-2-propanol

(b) 1-Ethylcyclohexanol

(c) 3-Phenyl-3-pentanol

(d) 2-Phenyl-2-pentanol

(e)

(f)
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