Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 3, Problem 4E
Consider the incomplete orbital representation of
a. Identify which lobes are hybrid orbitals (identify the type) and which lobes arep orbitals.
b. Use dotted lines to show any
c. Use up or down arrows to show electron occupation of each hybrid orbital or bond.
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Please answer this NEATLY, COMPLETELY, and CORRECTLY for an UPVOTE.
Determine the hybridization around C2 and nitrogen atoms.
What is the expected bond angle around C2 atoms?
Identify the type of bonds (σ or π) and the overlapping orbitals that form bonds A and B.
How would we modify the figure if we were looking at PH3 rather than NH3?
Answer the following questions about amoxicillin, an antibiotic from the penicillin family.
a. Predict the hybridization and geometry around each highlighted atom.
b. Label five polar bonds using the symbols δ+ and δ–.
c. How many π bonds does amoxicillin have? Label them.
d. Find a C – H bond containing a carbon atom having a hybrid orbital with 33% s-character
Chapter 3 Solutions
Organic Chemistry: A Guided Inquiry
Ch. 3 - Prob. 1CTQCh. 3 - What neutral atom is represented by the electron...Ch. 3 - Prob. 3CTQCh. 3 - Consider any one of the four identical hybrid...Ch. 3 - Prob. 5CTQCh. 3 - Prob. 6CTQCh. 3 - Prob. 7CTQCh. 3 - Prob. 8CTQCh. 3 - Prob. 9CTQCh. 3 - Prob. 10CTQ
Ch. 3 - On the left side of Figure 3.6, label the areas...Ch. 3 - Prob. 12CTQCh. 3 - Prob. 13CTQCh. 3 - Prob. 14CTQCh. 3 - Prob. 15CTQCh. 3 - Now consider the fully formed molecule on the...Ch. 3 - Prob. 1ECh. 3 - Explain why the two molecules below cannot...Ch. 3 - Prob. 3ECh. 3 - Consider the incomplete orbital representation of...Ch. 3 - Consider the following orbital representation of...Ch. 3 - Summarize how one determines the hybridization...Ch. 3 - Explain what is wrong with each of the following...Ch. 3 - Prob. 8ECh. 3 - Prob. 9ECh. 3 - Complete the following tables, and memorize their...Ch. 3 - Draw orbital representations of bonding in water...Ch. 3 - Draw electron configuration diagrams for carbon in...Ch. 3 - Prob. 13E
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- Now consider the fully formed molecule on the right side of Figure 3.7. a. Draw a Lewis structure of this molecule. b. Identify orbital representations of the two bonds and three bonds in Figure 3.7, andmatch these with representations of bonds on the Lewis structure you just drew.arrow_forwardUsing cartoon representations, draw a molecular orbital mixing diagram for a CO bond. In your picture, consider the relative energies of C and O and how this changes the resulting bonding and antibonding molecular orbitals relative to a CC bond.arrow_forwardA student draws the picture of ammonia (NH3) in the box below, left, and predicts it will be a flatmolecule with HNH bond angles of exactly 120°. Unfortunately, the student left something out. a. What did the student omit from his drawing? b. What is the actual HNH bond angle of ammonia (based on the draw g above, right)? c. Explain why water, ammonia, and methane (shown below) all have about the same bondangles (close to 109.5°) even though they have different numbers of bonds.arrow_forward
- For aspirin (acetylsalicylate), draw the complete structure, showing all atoms and bonds and including all lone pairs. b. Use a colored pencil/pen or highlighter and choose colors to denote sp3 , sp2and sp hybridized atoms. Mark all atoms (other than hydrogen) according to their hybridization. Please include a legend with your drawing letting me know which color corresponds to which hybridization state! C. Provide the chemical formula for your molecule The number of sigma and pie bondsarrow_forward3. Label the hybridization of any lone pair below that is an p orbital and provide a rationale for its hybridization. a. Abacavir - nucleoside reverse transcriptase inhibitor (anti-viral) used for the treatment of HIV/AIDS. НО. N OH O HN b. Doxycycline - A broad spectrum antibiotic with more than 8 million prescriptions given in the US every year. OH O OH|| 'N CH3 OH N NH₂ OH H3C CH3 NH₂arrow_forwardErythromycin (1), shown below, is an antibiotic medication which is employed in thetreatment of various bacterial infections. Answer parts i.-vii. on the molecule.i. Place lone pairs on the heteroatoms indicated by an arrow and a circle (A-B). il.Circle and label a sp3 hybridized atom with the letter C, and an atom with a trigonal planar geometry with the letter D. iii. State the number of chiral centres found in 1. Indicate, by clearly drawing on the molecule and labelling with the letter E, a tertiary (3º) hydrogen atom and the letter F a secondary (2º) hydrogen.V.Circle and label five different heteroatom-containing functional groups (not including the group circled) found in Erythromycin (1). Be sure to circle the entirefunctional group.vi. Underline the name of the most basic of the functional groups identified in v. above.vii. Identify one electrophilic carbon with a partial positive charge (o+). viii. Write down the molecular formula of compound 1.arrow_forward
- Please answer this NEATLY, COMPLETELY, and CORRECTLY for an UPVOTE. Determine the hybridization around C1, C2 and oxygen atoms. What is the expected bond angle around C1, and C2 atoms? Identify the type of bonds (σ or π) and the overlapping orbitals that form bonds A, B, and C.arrow_forwardA. Hybridization 1. Determine the hybridization of the nonhydrogen atoms in the following molecules. Note: you may want to complete (or fully interpret) the incomplete (condensed) Lewis structures first. H3C-NH2 H3C H3C CEN EN-NH2 O=C=O H3C H3C-OH H3C OH B. Dipole Moments 1. Indicate the direction of the dipole of each of the polar bonds in the following symmetrical molecules using the partial symbols, 5/5. If the molecules are polar, indicate their net dipoles using the dipole arrow, . O=C=0 F FIIC-F F 2. Indicate the direction of the dipole of each of the polar bonds in the following nonsymmetrical molecules using the partial symbols, 84/5. If the molecules are polar, indicate their net dipoles using the dipole arrow, +. H FIC-F H HIO HIC-F H H HIN-H H Farrow_forward2. The following questions apply to molecules X and Y. a. Determine the hybridisation of all atoms in the two molecules. b. Label each o bond, give the type of both orbitals (sp³, sp², sp or s) that make up the bond. Which orbitals are used to make up the bonds? c. Using your molecular model kit, choose atoms of the correct colour (white = H, black = C, blue = N and red = O) and correct shape for their hybridization (sp³ = 4 lobes, sp² = 5 lobes and sp= 6 lobes). Build the two models showing sigma bonds in grey and pi bonds in white. What are the angles around the central atom for sets of three atoms? O || H3C-C-CH3 and H₂C=C=CH₂ X Yarrow_forward
- E. Write the functional groups present in the following compound. Group A Group C Br yo Group E Br H ago K. Identify the atomic orbitals that overlap to form the marked bonds and the bond type. -O-CH,CH, Group D Identify the hybridization and bond angle of the marked atoms. Br O-CH,CH2TN. M. CH₂CH3 CH₂CH3 Group E N. -O-CH,CH2−N CH₂CH3 CH₂CH3 CH₂CH3 CH₂CH3arrow_forwardAnswer the following questions about amoxicillin, an antibiotic from the penicillin family. NH2 H N. HO НО amoxicillin a. Predict the hybridization and geometry around each highlighted atom. b. Label five polar bonds using the symbols &+ and &–. C. How many r bonds does amoxicillin have? Label them. d. Find a C – H bond containing a carbon atom having a hybrid orbital with 33% s-character.arrow_forward18. What type of bonds hold organic molecules together? How are they different than the bonds that hold inorganic molecules together? Be specific, I want more than just names of bonds. 19. For the following molecule draw in all the dipole moments using 6+ and 6. XX 20. BONUS: Why can an sp² hybridized carbon not form a double bond? 7arrow_forward
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