ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
6th Edition
ISBN: 9781266060144
Author: SMITH
Publisher: MCG
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Question
Chapter 10, Problem 60P
Interpretation Introduction
Interpretation: The mechanism for the formation of two constitutional isomers when
Concept introduction: The reaction of hydrogen halide with
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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.
None
Stereochemistry: Three possible answers- diastereomers, enantiomers
OH
CH₂OH
I
-c=0
21108 1101
41745 HOR
CH₂OH
IL
Но
CH₂OH
TIL
a. Compounds I and III have this relationship with each other: enantiomers
b. Compounds II and IV have this relationship with each other:
c. Compounds I and II have this relationship with each other:
d. *Draw one structure that is a stereoisomer of II, but neither a
diastereomer nor an enantiomer. (more than one correct answer)
Chapter 10 Solutions
ORGANIC CHEMISTRY - LOOSELEAF W/CONNECT
Ch. 10.1 - Prob. 1PCh. 10.2 - Problem 10.2 How many degrees of unsaturation are...Ch. 10.3 - Give the IUPAC name for each alkene. abcdeCh. 10.3 - Give the IUPAC name for each polyfunctional...Ch. 10.3 - Prob. 9PCh. 10.6 - Linolenic acidTable 10.2 and stearidonic acid are...Ch. 10.7 - Prob. 12PCh. 10.9 - Problem 10.13 What product is formed when each...Ch. 10.9 - Prob. 14PCh. 10.10 - Problem 10.15 Draw the products formed when each...
Ch. 10.10 - Prob. 16PCh. 10.10 - Prob. 17PCh. 10.10 - Addition of HBr to which of the following alkenes...Ch. 10.11 - Problem 10.19 Draw the products, including...Ch. 10.11 - Prob. 20PCh. 10.12 - Problem 10.21 What two alkenes give rise to each...Ch. 10.12 - Prob. 22PCh. 10.13 - Problem 10.23 Draw the products of each reaction,...Ch. 10.14 - Problem 10.24 Draw all stereoisomers formed in...Ch. 10.15 - Prob. 25PCh. 10.16 - Problem 10.26 What alkylborane is formed from...Ch. 10.16 - Draw the products formed when each alkene is...Ch. 10.16 - What alkene can be used to prepare each alcohol as...Ch. 10.16 - Prob. 29PCh. 10.17 - Draw the products of each reaction using the two...Ch. 10.18 - Problem 10.31 Devise a synthesis of each compound...Ch. 10 - Give the IUPAC name for each compound. a.b.Ch. 10 - a Label the carbon-carbon double bond in A as E or...Ch. 10 - Prob. 34PCh. 10 - 10.35 Calculate the number of degrees of...Ch. 10 - Prob. 36PCh. 10 - Label the alkene in each drug as E or Z....Ch. 10 - Give the IUPAC name for each compound. a. c. e. b....Ch. 10 - Prob. 39PCh. 10 - 10.40 (a) Draw all possible stereoisomers of, and...Ch. 10 - Prob. 41PCh. 10 - 10.42 Now that you have learned how to name...Ch. 10 - Prob. 43PCh. 10 - Prob. 44PCh. 10 - Prob. 45PCh. 10 - Draw the products formed when (CH3)2C=CH2 is...Ch. 10 - What alkene can be used to prepare each alkyl...Ch. 10 - Prob. 48PCh. 10 - Draw the constitutional isomer formed in each...Ch. 10 - Prob. 50PCh. 10 - Draw all stereoisomers formed in each reaction. a....Ch. 10 - Draw the products of each reaction, including...Ch. 10 - Prob. 53PCh. 10 - Draw a stepwise mechanism that shows how all three...Ch. 10 - Less stable alkenes can be isomerized to more...Ch. 10 - Prob. 60PCh. 10 - Prob. 61PCh. 10 - Bromoetherification, the addition of the elements...Ch. 10 - Devise a synthesis of each product from the given...Ch. 10 - 10.65 Draw a synthesis of each compound from...
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