ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
8th Edition
ISBN: 9780134595450
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 1.4, Problem 18P
a. Draw two Lewis structure for C2H6O.
b. Draw three Lewis structures for C3H8O.
(Hint: The two Lewis structures in part a are constitutional isomers—molecules that have the same atoms but differ in the way the atoms are connected. The three Lewis structures in part b are also constitutional isomers.)
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Complete boxes in the flow chart. Draw the structure of the organic compound foundin each layer after adding 3M NaOH and extraction. Make sure to include any charges. Provide explanation on answers.
==
Vid4Q2
Unanswered
☑
Provide IUPAC name of product in the reaction
below
A 3,4-dimethylcyclohexene
B 1,2-dimethylcyclohexane
C 1,2-dimethylcyclohexene
D 3,4-dimethylcyclohexane
H₂
Pd
5.
Use the MS data to answer the questions on the next page.
14.0
1.4
15.0
8.1
100-
MS-IW-5644
26.0
2.8
27.0
6.7
28.0
1.8
29.0
80
4.4
38.0
1.0
39.0
1.5
41.0
1.2
42.0
11.2
43.0
100.0
44.0
4.3
79.0
1.9
80.0
2.6
Relative Intensity
40
81.0
1.9
82.0
2.5
93.0
8.7
20-
95.0
8.2
121.0
2.0
123.0
2.0
136.0
11.8
0
138.0
11.5
20
40
8.
60
a.
Br
- 0
80
100
120
140
160
180
200
220
m/z
Identify the m/z of the base peak and molecular ion.
2
b.
Draw structures for each of the following fragments (include electrons and charges): 43.0, 93.0,
95.0, 136.0, and 138.0 m/z.
C.
Draw a reasonable a-fragmentation mechanism for the fragmentation of the molecular ion to
fragment 43.0 m/z. Be sure to include all electrons and formal charges.
6. Using the values provided in Appendix E of your lab manual, calculate the monoisotopic mass for the pyridinium
ion (CsH6N) and show your work.
Chapter 1 Solutions
ORGANIC CHEMISTRY-W/S.G+SOLN.MANUAL
Ch. 1.1 - Oxygen has three isotopes, 16O, 17O, and 18O. The...Ch. 1.1 - a. How many protons do the following species...Ch. 1.1 - Chlorine has two isotopes, 35Cl and 37Cl; 75.77%...Ch. 1.2 - Prob. 4PCh. 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. 16PCh. 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. 20PCh. 1.4 - Which of the atoms in the molecular models in...Ch. 1.4 - Prob. 22PCh. 1.4 - Prob. 23PCh. 1.5 - Draw the following orbitals: a. 3s orbital b. 4s...Ch. 1.6 - Prob. 25PCh. 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. 1.9 - For each of the given species: a. Draw its Lewis...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. 35PCh. 1.13 - a. What are the relative lengths and strengths of...Ch. 1.13 - Prob. 38PCh. 1.14 - Describe the orbitals used in bonding and the bond...Ch. 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 - a. What is the hybridization of each of the carbon...Ch. 1.15 - Predict the approximate bond angles for a. the CNC...Ch. 1.16 - What of the following molecules would you expect...Ch. 1.16 - Account for the difference in the shape and color...Ch. 1.16 - If the dipole moment of CH3F is 1.847 D and the...Ch. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - Prob. 50PCh. 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. 54PCh. 1 - Draw a Lewis structure for each of the following:...Ch. 1 - What is the hybridization of each of the carbon...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 - Prob. 59PCh. 1 - What is the hybridization of the indicated atom in...Ch. 1 - Predict the approximate bond angles for the...Ch. 1 - Prob. 62PCh. 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 - Prob. 67PCh. 1 - Rank the following compounds from highest dipole...Ch. 1 - In which orbitals are the lone pairs in nicotine?Ch. 1 - Prob. 70PCh. 1 - Prob. 71PCh. 1 - a. Which of the species have bond angles of 109.5?...Ch. 1 - Prob. 73PCh. 1 - Which compound has a larger dipole moment: CH3Cl...Ch. 1 - Prob. 75PCh. 1 - Explain why CH3Cl has a greater dipole moment than...Ch. 1 - a. Draw a Lewis structure for each of the...Ch. 1 - There are three isomers with molecular formula...
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