ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 20, Problem 20.1P
Interpretation Introduction

(a)

Interpretation: The orbitals are used to form the indicated bonds in α- sinensal are to be predicted.

Concept introduction: α- sinensal is a weak base and insoluble in water. It is a constituent of orange oil. The molecular formula of α- sinensal is C15H22O and its IUPAC name is (2E, 6E, 9E)-2, 6, 10-trimethyl-2, 6, 9, 11-dodecatetraenal.

Expert Solution
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Answer to Problem 20.1P

The orbitals are used to form bond [1], bond [2] and bond [3] are sp2 hybrid orbitals.

Explanation of Solution

The given structure of α- sinensal is,

ORGANIC CHEMISTRY, Chapter 20, Problem 20.1P

Figure 1

Bond [1] is formed by the overlapping of sp2 hybrid orbitals of carbonyl carbon with sp2 hybrid orbitals of adjacent carbon. Hence, the orbitals are used to form bond [1] are sp2 hybrid orbitals.

Bond [2] indicates the double bond between carbon and oxygen i.e. carbonyl bond in which one bond is pi and other one is sigma bond. The pi bond is formed by the lateral overlapping of unhybridized 2p orbital of carbon with 2p orbital of oxygen. The sigma bond is formed by head to head overlapping of sp2 hybrid orbitals of oxygen atom and sp2 hybrid orbitals of carbon atom. Hence, the orbitals are used to form bond [2] are sp2 hybrid orbitals.

Bond [3] is formed by the overlapping of sp2 hybrid orbitals of carbon atom with sp2 hybrid orbitals of adjacent carbon atom. Hence, the orbitals are used to form bond [3] are sp2 hybrid orbitals.

Conclusion

The orbitals are used to form bond [1], bond [2] and bond [3] are sp2 hybrid orbitals.

Interpretation Introduction

(b)

Interpretation: The type of orbitals where the lone pairs on O reside are to be predicted.

Concept introduction: α- sinensal is a weak base and insoluble in water. It is a constituent of orange oil. The molecular formula of α- sinensal is C15H22O and its IUPAC name is (2E, 6E, 9E)-2, 6, 10-trimethyl-2, 6, 9, 11-dodecatetraenal.

Expert Solution
Check Mark

Answer to Problem 20.1P

The type of orbitals where the lone pairs on O reside are 2s and 2p orbitals.

Explanation of Solution

The oxygen atom of carbonyl carbon in α- sinensal has two lone pairs. One of the lone pair of electrons is located in the 2s orbital and other one is located on the 2p orbitals of oxygen atom. Hence, the type of orbitals where the lone pairs on O reside are 2s and 2p orbitals.

Conclusion

The type of orbitals where the lone pairs on O reside are 2s and 2p orbitals.

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Chapter 20 Solutions

ORGANIC CHEMISTRY

Ch. 20 - Prob. 20.11PCh. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - Prob. 20.15PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Prob. 20.19PCh. 20 - Prob. 20.20PCh. 20 - Problem 20.21 Draw the product of each reaction. ...Ch. 20 - Problem 20.22 Draw the products (including...Ch. 20 - Problem 20.23 What Grignard reagent and carbonyl...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - Problem 20.28 What ester and Grignard reagent are...Ch. 20 - Prob. 20.29PCh. 20 - Problem 20.30 What reagent is needed to convert ...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Problem 20.34 Draw the product when each compound...Ch. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - 20.39 Draw the product formed when is treated...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.41PCh. 20 - 20.42 Draw the products or each reduction...Ch. 20 - Prob. 20.43PCh. 20 - 20.44 Draw all stereoisomers formed in each...Ch. 20 - Prob. 20.45PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.48PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.50PCh. 20 - 20.51 Draw a stepwise mechanism for the following...Ch. 20 - 20.52 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.53PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.55PCh. 20 - Prob. 20.56PCh. 20 - 20.57 What ester and Grignard reagent are needed...Ch. 20 - 20.58 What organolithium reagent and carbonyl...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.60PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - 20.62 Synthesize each compound from cyclohexanol...Ch. 20 - 20.63 Convert propan-2-ol into each compound....Ch. 20 - 20.64 Convert benzene into each compound. You may...Ch. 20 - 20.65 Design a synthesis of each compound from...Ch. 20 - 20.66 Synthesize each compound from the given...Ch. 20 - Prob. 20.67PCh. 20 - Prob. 20.68PCh. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - 20.74 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.75PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - Prob. 20.79PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.81P
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