Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 1, Problem 1.37P
Citric acid is responsible for the tartness of citrus fruits, especially lemons and limes.
a. What is the molecular formula of citric acid?
b. How many lone pairs are present?
c. Draw a skeletal structure.
d. How many
e. What orbitals are used to form each indicated bond
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
a) Consider a molecule of acetone cyanohydrin, shown below. What is the hybridization and molecular geometry at CA, CB, and O?
(b) For Carbon B (CB) and nitrogen (N), draw orbital energy diagrams showing the orbitals involved in bonding after hybridization. Be sure to fill the orbitals appropriately with valence electrons.
c) In your diagrams in part (b), which orbitals are involved in sigma and pi bonding?
Orbitals Involved in Sigma Bonding Orbitals Involved in Pi Bonding
2p
sp
sp2
sp3
2p
sp
sp2
sp3
(d) In a sample containing many molecules of acetone cyanohydrin (and no other substances), what type(s) of intermolecular forces could be present? Choose all that apply. Covalent Bonds Hydrogen Bonds Dipole-Dipole Forces London Dispersion Forces
What is the hybrid orbital of C in 4 single bonds? in 1 double bond and 2 single bonds? In 1 triple bond and 1 single bond [≡C-]? In 2 double bonds [=C=]?
1. Calculate the percentage s and p characters in sp, sp^2 and sp^3 hybrid orbitals.
2. Draw the molecular orbital diagram of propene, CH3-CH=CH2.
3. Draw an orbital diagram of an allene, H2C=C=CH2. What hybridization must the central carbon atom have in order to form two double bonds?
4. Describe the shape of sp^3 hybrid orbitals.
5. Dicuss, with illustrations, the two main steps in the hybridization of a carbon atom.
6.a. Arrange the following organic molecules in order of increasing acidity, starting with the least acidic.
CH3CH3, HC(=_)CH and CH2=CH2
b. How many hybrid orbitals are formed when one 2s atomic orbital mixes with two 2p atomic orbitals? What shape do they form?
c. Describe in detail, the shape of p atomic orbitals.
d. Giving an example, explain what is meant by the excited-state electronic configuration of an atom of an element.
e. Using clear illustrations, discuss the main differences between E1 and E2 mechanisms in organic reactions.
Chapter 1 Solutions
Organic Chemistry
Ch. 1 - While the most common isotope of nitrogen has a...Ch. 1 - Label each bond in the following compounds as...Ch. 1 - How many covalent bonds are predicted for each...Ch. 1 - Draw a valid Lewis structure for each species. a....Ch. 1 - Draw an acceptable Lewis structure for each...Ch. 1 - Prob. 1.6PCh. 1 - Draw a Lewis structure for each ion. a. CH3Ob....Ch. 1 - Draw Lewis structures for each molecular formula....Ch. 1 - Prob. 1.9PCh. 1 - Prob. 1.10P
Ch. 1 - Prob. 1.11PCh. 1 - Prob. 1.12PCh. 1 - Draw a second resonance structure for each...Ch. 1 - Prob. 1.14PCh. 1 - Draw a second resonance structure for nitrous...Ch. 1 - Prob. 1.16PCh. 1 - Prob. 1.17PCh. 1 - Prob. 1.18PCh. 1 - Prob. 1.19PCh. 1 - Prob. 1.20PCh. 1 - Simplify each condensed structure by using...Ch. 1 - Prob. 1.22PCh. 1 - Prob. 1.23PCh. 1 - Convert each skeletal structure to a complete...Ch. 1 - Draw in all hydrogens and lone pairs on the...Ch. 1 - Prob. 1.26PCh. 1 - What orbitals are used to form each of the CC, and...Ch. 1 - What orbitals are used to form each bond in the...Ch. 1 - Determine the hybridization around the highlighted...Ch. 1 - Classify each bond in the following molecules as ...Ch. 1 - Prob. 1.31PCh. 1 - Rank the following atoms in order of increasing...Ch. 1 - Prob. 1.33PCh. 1 - Prob. 1.34PCh. 1 - Provide the following information about...Ch. 1 - Use the ball-and-stick model to answer each...Ch. 1 - Citric acid is responsible for the tartness of...Ch. 1 - Zingerone gives ginger its pungent taste. a.What...Ch. 1 - Two radioactive isotopes of iodine used for the...Ch. 1 - Prob. 1.40PCh. 1 - Assign formal charges to each carbon atom in the...Ch. 1 - Assign formal charges to each N and O atom in the...Ch. 1 - Draw one valid Lewis structure for each compound....Ch. 1 - Prob. 1.44PCh. 1 - Prob. 1.45PCh. 1 - Prob. 1.46PCh. 1 - Draw all possible isomers for each molecular...Ch. 1 - 1.45 Draw Lewis structures for the nine isomers...Ch. 1 - Prob. 1.49PCh. 1 - Prob. 1.50PCh. 1 - Prob. 1.51PCh. 1 - Prob. 1.52PCh. 1 - Prob. 1.53PCh. 1 - Prob. 1.54PCh. 1 - Draw all reasonable resonance structures for each...Ch. 1 - Prob. 1.56PCh. 1 - Rank the resonance structures in each group in...Ch. 1 - 1.56 Consider the compounds and ions with curved...Ch. 1 - 1.57 Predict all bond angles in each...Ch. 1 - Predict the geometry around each indicated atom....Ch. 1 - Prob. 1.61PCh. 1 - Prob. 1.62PCh. 1 - Draw in all the carbon and hydrogen atoms in each...Ch. 1 - Prob. 1.64PCh. 1 - Prob. 1.65PCh. 1 - Prob. 1.66PCh. 1 - Prob. 1.67PCh. 1 - Each of the following condensed or skeletal...Ch. 1 - Prob. 1.69PCh. 1 - Prob. 1.70PCh. 1 - Prob. 1.71PCh. 1 - Prob. 1.72PCh. 1 - Prob. 1.73PCh. 1 - Prob. 1.74PCh. 1 - Two useful organic compounds that contain Cl atoms...Ch. 1 - Use the symbols + and to indicate the polarity of...Ch. 1 - Label the polar bonds in each molecule. Indicate...Ch. 1 - Answer the following questions about acetonitrile...Ch. 1 - Prob. 1.79PCh. 1 - The principles of this chapter can be applied to...Ch. 1 -
a. What is the hybridization of each N atom in...Ch. 1 - 1.77 Stalevo is the trade name for a medication...Ch. 1 - 1.78 and are two highly reactive carbon...Ch. 1 - 1.79 The N atom in (acetamide) is hybridized,...Ch. 1 - Prob. 1.85PCh. 1 - Prob. 1.86PCh. 1 - Prob. 1.87PCh. 1 - Prob. 1.88PCh. 1 - Prob. 1.89PCh. 1 - Prob. 1.90P
Additional Science Textbook Solutions
Find more solutions based on key concepts
For Practice 1.1
Is each change physical or chemical? Which kind of property (chemical or physical) is demonst...
Principles of Chemistry: A Molecular Approach (3rd Edition)
Fully developed conditions are known to exist for water flowing through a 25-nim-diameer tube at 0.01 kg/s and ...
Fundamentals of Heat and Mass Transfer
Label each statement about the polynucleotide ATGGCG as true or false. The polynucleotide has six nucleotides. ...
General, Organic, & Biological Chemistry
Practice Exercise 1
Which of the following factors determines the size of an atom? a. the volume of the nucleus...
Chemistry: The Central Science (13th Edition)
Determine the number of protons, neutrons, and electrons in the following atoms: a. a hydrogen atom that has a ...
General, Organic, and Biological Chemistry (3rd Edition)
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- Consider the following computer-generated model of caffeine: Complete a Lewis structure for caffeine in which all atoms have a formal charge of zero (as is typical with most organic compounds). How many C and N atoms are sp2 hybridized? How many C and N atoms are sp3 hybridized? sp hybridized? How many and bonds are there?arrow_forwardExplain what is wrong with each of the following statements. a. “A bond is a double bond. b. “A bond consists of four electrons, one in each of the four p orbitals involved in the bond. c. “A bond is twice as strong as a bond because it consists of two orbital overlaps insteadof just one.”arrow_forwardIn the hydrocarbon(a) What is the hybridization at each carbon atom in themolecule? (b) How many s bonds are there in the molecule?(c) How many p bonds? (d) Identify all the 120° bond anglesin the molecule. [Section 9.6]arrow_forward
- - What orbital(s) are the lone pairs of electrons on the O atom placed? - What orbital is the lone pair of electrons on the N atom placed? - What type of bond(s) are formed between Ca1 – C? - What type of bond(s) are formed between C = O? - What type of bond(s) are formed between C – N? - What type of bond(s) are formed between N – Ca2? - What type of bond(s) are formed between N – H? - What is the angle between Ca1 – C = O? - What is the angle between Ca1 – C – N? - What is the angle between O = C – N? - What is the angle between C – N – Ca2?arrow_forwardOne of the first drugs to be approved for use in treatment of acquired immune deficiency syndrome (AIDS) was azidothymidine (AZT). Complete the Lewis structure for AZT. a. How many carbon atoms are sp3 hybridized? b. How many carbon atoms are sp2 hybridized? c. Which atom is sp hybridized? d. How many σ bonds are in the molecule? e. How many π bonds are in the molecule? f. Wnat isthe N9N9N bond angle inthe azide (-N3) group? g. What is the H-Q-C bond angle in the side group attached to the five membered ring? h. What is the hybridization of the oxygen atom in the -CH2OH group?arrow_forwardFill in each blank sentence with numbers 0-10. An sp3-hybridized atom possess _____ s orbital(s), _______ p orbital(s), and _____ hybrid orbital(s) in its valence shell. Such an atom can form up to _____ sigma bonds and _____ pi bonds.arrow_forward
- One of the first drugs to be approved for use in treatment of acccquired immune deficiency syndrome (AIDS) was azidothymidine (AZT). Complete the Lewis structure for AZT a. How many carbon atoms are sp3 hybridised? b. How many carbon atoms are sp2 hybridised? c. Which atom is sp hybridised? d. How many σ bonds are in the molecule? e. How many π bonds are in the molecule? f. What is the N9N9N bond angle in the azide (--N3) group? g. What is the H--Q--C bond angle in the side group attached to the five-membered ring? h. What is the hybridization of the oxygen atom in the --CH2OH group?arrow_forwardDraw orbital diagrams (boxes with arrows in them) to represent the electron configurations—without hybridization—for all the atoms in SF2. Circle the electrons involved in bonding. Draw a three-dimensional sketch of the molecule and show orbital overlap. What bond angle do you expect from the unhybridized orbitals? How well does valence bond theory agree with theexperimentally measured bond angle of 98.2°?arrow_forwardWhat are the hybridizations of carbon atoms 1, 2, and 3 shown in the model below? H2C = CH - CH3 a. sp 2, sp 2, sp 3 b. sp, sp, sp 2 c. sp2, sp, sp 3 d. sp, sp 2, sp 2arrow_forward
- How many sp2 hybridized carbons are present?arrow_forwardHow many pi bonds? How many unhybridized p-orbitals? How many sp-orbitals? How many sp2-orbitals?arrow_forward1. How many sp^3 orbitals does your oxygen have? * 2. How many Pi bond/s connect/s your Oxygen to your Carbon? * 3. How many sigma bond/s connect/s your Oxygen to your Carbon? * 4. Which line representation would tell the viewer of which hydrogen is toward him/her (closest to the viewer)? *A. AB. BC. CD. None of the above 5. What hybrid orbital do all your central atoms have? *A. spB. sp^2C. sp^3D. spd^3 6. If we are to consider only your C-O-C, what geometry will they form? *A. tetrahedralB. trigonal pyramidalC. trigonal planarD. linearE. bent 7. What angle will be closest to the angle of number 1? *A. 180B. 109.5C. 120D. 90 8. What angle will be closest to the angle of number 2? *A. 180B. 109.5C. 120D. 90 9. How many hybrid orbitals that formed covalent bonds can you count? *1 pointA. 6B. 7C. 8D. 9E. 10F. 11 10. How many atoms were bonded covalently? *arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
Chemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
Chemistry: Principles and PracticeChemistryISBN:9780534420123Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward MercerPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry: An Atoms First Approach
Chemistry
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Cengage Learning
Chemistry: Principles and Practice
Chemistry
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Cengage Learning
Stoichiometry - Chemistry for Massive Creatures: Crash Course Chemistry #6; Author: Crash Course;https://www.youtube.com/watch?v=UL1jmJaUkaQ;License: Standard YouTube License, CC-BY
Bonding (Ionic, Covalent & Metallic) - GCSE Chemistry; Author: Science Shorts;https://www.youtube.com/watch?v=p9MA6Od-zBA;License: Standard YouTube License, CC-BY
General Chemistry 1A. Lecture 12. Two Theories of Bonding.; Author: UCI Open;https://www.youtube.com/watch?v=dLTlL9Z1bh0;License: CC-BY