EBK ORGANIC CHEMISTRY
7th Edition
ISBN: 9780133556186
Author: Bruice
Publisher: VST
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Chapter 1, Problem 63P
Rank the following compounds from highest dipole moment to lowest dipole moment:
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EEZE
LETCHUP
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Draw the most likely conjugate base resulting from this acid-base reaction.
Include all lone pairs. Ignore inorganic byproducts.
Drawing
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NaOCH2CH3
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Answer
2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton
transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted
without ambiguity.
a.
CH3
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OEt
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Ph
CH3
Hint: the species on the left is an ynolate, which behaves a lot like an enolate.
Chapter 1 Solutions
EBK ORGANIC CHEMISTRY
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.1 - Chlorine has two isotopes, 35Cl and 37Cl; 75.77%...Ch. 1.2 - Prob. 3PCh. 1.2 - a. Write the ground-state electronic configuration...Ch. 1.2 - Look at the relative positions of each pair of...Ch. 1.3 - a. Find potassium (K) in the periodic table and...Ch. 1.3 - Which bond is more polar? a. b. c. d.Ch. 1.3 - Which of the following has a. the most polar bond?...Ch. 1.3 - Use the symbols + and to show the direction of...Ch. 1.3 - Explain why HCL has a smaller dipole moment than...
Ch. 1.3 - After examining the potential maps for LiH, HF,...Ch. 1.4 - An atom with a formal charge does not necessarily...Ch. 1.4 - Prob. 15PCh. 1.4 - a. Draw two Lewis structure for C2H6O. b. Draw...Ch. 1.4 - Draw the lone-pair electrons that are not shown in...Ch. 1.4 - Prob. 19PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 21PCh. 1.5 - Draw the following orbitals: a. 3s orbital b. 4s...Ch. 1.6 - Prob. 23PCh. 1.6 - Indicate the kind of molecular orbital (, , , or )...Ch. 1.7 - What orbitals are used to form the 10 sigma bonds...Ch. 1.7 - Explain why a bond formed by overlap of s orbital...Ch. 1.9 - Put n number in each of the blanks: a. __ s...Ch. 1.11 - Predict the approximate bond angles in a. the...Ch. 1.11 - According to the potential map for the ammonium...Ch. 1.12 - Prob. 32PCh. 1.13 - a. What are the relative lengths and strengths of...Ch. 1.13 - Prob. 35PCh. 1.14 - Prob. 36PCh. 1.15 - Which of the bond in a carbon-oxygen double bond...Ch. 1.15 - Would you expect a CC bond formed by sp2sp2...Ch. 1.15 - Caffeine is a natural insecticide found in the...Ch. 1.15 - Prob. 41PCh. 1.15 - Predict the approximate bond angles for a. the CNC...Ch. 1.16 - If the dipole moment of CH3F is 1.847 D and the...Ch. 1.16 - Account for the difference in the shape and color...Ch. 1.16 - What of the following molecules would you expect...Ch. 1 - Prob. 46PCh. 1 - Prob. 47PCh. 1 - What is the hybridization of all the atoms (other...Ch. 1 - Draw the condensed structure of a compound that...Ch. 1 - Predict the approximate bond angles: a. the CNH...Ch. 1 - Prob. 51PCh. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - 53. What is the hybridization of each of the...Ch. 1 - Rank the bonds from most polar. a. CO, CF, CN b....Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Prob. 57PCh. 1 - Prob. 58PCh. 1 - Draw the missing lone-pair electrons and assigns...Ch. 1 - a. Which of the indicated bonds in each molecule...Ch. 1 - For each of the following molecules, indicate the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Rank the following compounds from highest dipole...Ch. 1 - In which orbitals are the lone pairs in nicotine?Ch. 1 - Prob. 65PCh. 1 - Prob. 66PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 68PCh. 1 - Which compound has a larger dipole moment: CH3Cl...Ch. 1 - Prob. 70PCh. 1 - Prob. 71PCh. 1 - Explain why CH3Cl has a greater dipole moment than...Ch. 1 - Prob. 73P
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- 1. For each of the reaction "railroads" below, you are either asked to give the structure(s) of the starting material(s) or product(s), or provide reagents/conditions to accomplish the transformation, as indicated by the boxes. a. NaOMe H+ .CO,H HO₂C MeOH (excess) MeOH H3C Br يع CH3 1. LiAlH4 2. H3O+ 3. PBг3 H3C 1. Et-Li 2. H3O+ -CO₂Me -CO₂Me OH CH3 CH3 ল CH3arrow_forwardPredict the intermediate 1 and final product 2 of this organic reaction: NaOMe ག1, ད།་, - + H You can draw 1 and 2 in any arrangement you like. 2 work up Note: if either 1 or 2 consists of a pair of enantiomers, just draw one structure using line bonds instead of 3D (dash and wedge) bonds at the chiral center. Explanation Check Click and drag to start drawing a structure. Х © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Parrow_forwardWhat is the total energy cost associated with the compound below adopting the shown conformation? CH3 HH DH CH3arrow_forward
- ΗΝ, Draw Final Product C cyclohexanone pH 4-5 Edit Enamine H3O+ CH3CH2Br THF, reflux H Edit Iminium Ionarrow_forwardHow many hydrogen atoms are connected to the indicated carbon atom?arrow_forwardIdentify the compound with the longest carbon - nitrogen bond. O CH3CH2CH=NH O CH3CH2NH2 CH3CH2C=N CH3CH=NCH 3 The length of all the carbon-nitrogen bonds are the samearrow_forward
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