Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Biacetyl and acetoin are added to margarine to make it taste more like butter. Complete the Lewis structures, predict values for all \(\mathrm{C}-\mathrm{C}-\mathrm{O}\) bond angles, and give the hybridization of the carbon atoms in these two compounds. Must the four carbon atoms and two oxygen atoms in biacetyl lie the same plane? How many \(\sigma\) bonds and how many \(\pi\) bonds are there in biacetyl and acetoin?

Short Answer

Expert verified
In both biacetyl and acetoin, the C-C-O bond angles are approximately \(120^\circ\). The hybridization is sp^2 for the carbonyl carbon atoms and sp^3 for other carbon atoms involved in single bond formation. In biacetyl, all carbon and oxygen atoms lie in the same plane, while the σ bonds and π bonds are: 8 σ and 2 π for biacetyl, and 10 σ and 1 π for acetoin.

Step by step solution

01

Bond angles in biacetyl

In biacetyl, there are two C-C-O bond angles. Both consist of a sp^2 hybridized carbon atom (C=O) connected to an sp^3 hybridized carbon atom (C-C). This results in a bond angle of approximately 120°. Therefore, both C-C-O bond angles in biacetyl are \(\sim 120^\circ\).
02

Bond angles in acetoin

In acetoin, there is only one C-C-O bond angle. The sp^2 hybridized carbon atom (C=O) is connected to an sp^3 hybridized carbon atom (C-OH). As a result, the bond angle is approximately 120°. Therefore, the C-C-O bond angle in acetoin is \(\sim 120^\circ\). ## Step 3: Determine the hybridization of the carbon atoms ##
03

Hybridization in biacetyl

In biacetyl, the two carbonyl carbon atoms have sp^2 hybridization. The other two carbon atoms involved in single bond formation have sp^3 hybridization.
04

Hybridization in acetoin

In acetoin, the carbonyl carbon atom has sp^2 hybridization. The other carbon atom involved in the single bond formation (C-OH) has sp^3 hybridization. ## Step 4: Determine if the four carbon atoms and two oxygen atoms in biacetyl all lie in the same plane ##
05

Planarity in biacetyl

In biacetyl, all four carbon atoms and two oxygen atoms lie in the same plane because each carbonyl carbon atom has sp^2 hybridization, resulting in a flat, planar molecular structure. ## Step 5: Count the number of sigma (σ) bonds and pi (π) bonds ##
06

Number of σ and π bonds in biacetyl

In biacetyl, there are 8 σ bonds (6 C-H, 1 C-C, and 1 O-C) and 2 π bonds (2 C=O). Total: σ bonds = 8, π bonds = 2
07

Number of σ and π bonds in acetoin

In acetoin, there are 10 σ bonds (6 C-H, 2 C-C, 1 O-C, and 1 O-H) and 1 π bond (1 C=O). Total: σ bonds = 10, π bonds = 1

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.

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

Acetylene \(\left(\mathrm{C}_{2} \mathrm{H}_{2}\right)\) can be produced from the reaction of calcium carbide \(\left(\mathrm{CaC}_{2}\right)\) with water. Use both the localized electron and molecular orbital models to describe the bonding in the acetylide anion \(\left(\mathrm{C}_{2}^{2-}\right)\)

What are the relationships among bond order, bond energy, and bond length? Which of these quantities can be measured?

Show how a hydrogen \(1 s\) atomic orbital and a fluorine \(2 p\) atomic orbital overlap to form bonding and antibonding molecular orbitals in the hydrogen fluoride molecule. Are these molecular orbitals \(\sigma\) or \(\pi\) molecular orbitals?

Why are \(d\) orbitals sometimes used to form hybrid orbitals? Which period of elements does not use \(d\) orbitals for hybridization? If necessary, which \(d\) orbitals \((3 d, 4 d, 5 d\), or \(6 d)\) would sulfur use to form hybrid orbitals requiring \(d\) atomic orbitals? Answer the same question for arsenic and for iodine.

In Exercise 89 in Chapter 8, the Lewis structures for benzene \(\left(\mathrm{C}_{6} \mathrm{H}_{6}\right)\) were drawn. Using one of the Lewis structures, estimate \(\Delta H_{\mathrm{f}}^{\circ}\) for \(\mathrm{C}_{6} \mathrm{H}_{6}(g)\) using bond energies and given that the standard enthalpy of formation of \(\mathrm{C}(g)\) is \(717 \mathrm{~kJ} / \mathrm{mol}\). The experimental \(\Delta H_{\mathrm{f}}^{\circ}\) value of \(\mathrm{C}_{6} \mathrm{H}_{6}(g)\) is \(83 \mathrm{~kJ} / \mathrm{mol} .\) Explain the discrepancy between the experimental value and the calculated \(\Delta H_{\mathrm{f}}^{\circ}\) value for \(\mathrm{C}_{6} \mathrm{H}_{6}(g)\)

See all solutions

Recommended explanations on Chemistry Textbooks

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