If you like us, please share us on social media.
The latest UCD Hyperlibrary newsletter is now complete, check it out.

GeoWiki.png
ChemWiki: The Dynamic Chemistry E-textbook > Organic Chemistry > Organic Chemistry With a Biological Emphasis > Chapter 1: Introduction to organic structure and bonding I > Section 1.P: Problems for Chapter 1

MindTouch
Copyright (c) 2006-2014 MindTouch Inc.
http://mindtouch.com

This file and accompanying files are licensed under the MindTouch Master Subscription Agreement (MSA).

At any time, you shall not, directly or indirectly: (i) sublicense, resell, rent, lease, distribute, market, commercialize or otherwise transfer rights or usage to: (a) the Software, (b) any modified version or derivative work of the Software created by you or for you, or (c) MindTouch Open Source (which includes all non-supported versions of MindTouch-developed software), for any purpose including timesharing or service bureau purposes; (ii) remove or alter any copyright, trademark or proprietary notice in the Software; (iii) transfer, use or export the Software in violation of any applicable laws or regulations of any government or governmental agency; (iv) use or run on any of your hardware, or have deployed for use, any production version of MindTouch Open Source; (v) use any of the Support Services, Error corrections, Updates or Upgrades, for the MindTouch Open Source software or for any Server for which Support Services are not then purchased as provided hereunder; or (vi) reverse engineer, decompile or modify any encrypted or encoded portion of the Software.

A complete copy of the MSA is available at http://www.mindtouch.com/msa

Section 1.P: Problems for Chapter 1

Table of Contents

link to Solutions Manual

 

P1.1: Draw a picture showing the orbitals involved in bonding in the molecules below.  Draw all bonds, both sigma and pi, as overlapping orbitals.  Locate all lone pairs in their appropriate orbitals. 

a) dimethyl ether (CH3OCH3)

b) ethanol (CH3CH2OH)

c) acetaldehyde (CH3COH)

d) hydrogen cyanide (HCN)

P1.2:  Give the electron configuration for:

a) a lithium cation (Li+)

b) a calcium cation (Ca2+)

c) a iron cation in the ferric (Fe+3) state

P1.3: Draw one example each (there are many possible correct answers) of compounds fitting the descriptions below, using line structures.  Be sure to designate the location of all non-zero formal charges. All atoms should have complete octets (phosphorus may exceed the octet rule).

a) an 8-carbon molecule with secondary alcohol, primary amine, amide, and cis-alkene groups

b) a 12-carbon molecule with carboxylate, diphosphate, and lactone (cyclic ester) groups.

c) a 9-carbon molecule with cyclopentane, trans-alkene, ether, and aldehyde groups

P1.4: For the structures below, label all non-zero formal charges, and determine the molecular formula and the IHD.

image224.png

P1.5: In the structures shown below:

a-i) Describe the orbitals involved in the bonds indicated by the arrows. 

j) Fill in all formal charges

k) Give the molecular formula for arginine

image226.png

image228.png

P1.6: The four compounds below appeared in the October 9 and October 25, 2006 issues of Chemical and Engineering News. 

a-k) For each bond indicated by an arrow, specify the types of orbitals that are overlapping.

l) Which compound contains two aldehydes?  Which contains an ether?  Which contains an amide? Which contains a terminal alkene? Which contains an amine (and is this amine primary, secondary, tertiary, or quaternary?)

m) Give the molecular formula for compound 3

image230.png

P1.7: Draw four isomers with the molecular formula C4H8. (

P1.8: Draw structures of four different amides with molecular formula C3H7NO.

P1.9: Rank the bonds a-f below according to increasing bond length.

image232.png

P1.10: Draw the structures of the following organic molecules:

a) 2,6-dimethyldecane

b) 2,2,5,5-tetramethyl-3-hexanol

c) methyl butanoate

d) N-ethylhexanamide

e) 7-fluoroheptanoate

f) ) 1-ethyl-3,3-dimethylcyclohexene

Challenge problems

C1.1: Imagine that you hear a description of the bonding in water as being derived directly from the atomic orbital theory, without use of the hybrid orbital concept.  In other words, the two bonds would be formed by the overlap of the half-filled 2py and 2pz orbitals of oxygen with the 1s orbitals of hydrogen, while the two lone pairs on oxygen would occupy the 2s and 2px orbitals.  What is wrong with this picture?  How would the bonding geometry differ from what is actually observed for water?

C1.2: Draw a picture showing the geometry of the overlapping orbitals that form the bonding network in allene, H2CCCH2.  Then, draw a Lewis structure for the molecule, using the solid/dash wedge bond convention as necessary to indicate the correct geometry of the s bonds.

 

Contributors

You must to post a comment.
Last Modified
08:31, 2 Oct 2013

Tags

Classifications

Vet5
Lower Divisional

Creative Commons License Unless otherwise noted, content in the UC Davis ChemWiki is licensed under a Creative Commons Attribution-Noncommercial-Share Alike 3.0 United States License. Permissions beyond the scope of this license may be available at copyright@ucdavis.edu. Questions and concerns can be directed toward Prof. Delmar Larsen (dlarsen@ucdavis.edu), Founder and Director. Terms of Use