ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Textbook Question
Chapter 6.11B, Problem 6.19P
For each pair of compounds, state which compound is the better SN2 substrate.
- a. 2-methyl-1-iodopropane or tert-butyl iodide
- b. cyclohexyl bromide or 1-bromo-1-methylcydohexane
- c.2 bromobutane or isopropyl bromide
- d. 1-chloro-2,2-dimethylbutane or2-chlorobutane
- e.1-iodobutane or 2-iodopropane
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Predict the intermediate 1 and final product 2 of this organic reaction:
NaOMe
H+
+
1
2
H
H
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You can draw 1 and 2 in any arrangement you like.
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.
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X
$
dm
Predict the major products of this organic reaction:
1. NaH (20°C)
2. CH3Br
?
Some notes:
• Draw only the major product, or products. You can draw them in any arrangement you like.
• Be sure to use wedge and dash bonds where necessary, for example to distinguish between major products that are enantiomers.
• If there are no products, just check the box under the drawing area.
No reaction.
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G
Cr
Predict the major products of this organic reaction:
1. LDA (-78°C)
?
2. Br
Some notes:
• Draw only the major product, or products. You can draw them in any arrangement you like.
.
• Be sure to use wedge and dash bonds where necessary, for example to distinguish between major products that are enantiomers.
• If there are no products, just check the box under the drawing area.
No reaction.
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X
Chapter 6 Solutions
ORGANIC CHEMISTRY
Ch. 6.1 - Classify each compound as an alkyl halide, a vinyl...Ch. 6.2 - Give the structures of the following compounds. a....Ch. 6.2 - For each of the following compounds, A. give the...Ch. 6.3E - Prob. 6.4PCh. 6.4 - Prob. 6.5PCh. 6.5A - For each pair of compounds, predict which compound...Ch. 6.5B - Prob. 6.7PCh. 6.6B - Prob. 6.8PCh. 6.6B - The light-initiated reaction of...Ch. 6.6B - Show how free-radical halogenation might be used...
Ch. 6.7 - Prob. 6.11PCh. 6.7 - Prob. 6.12PCh. 6.8 - Prob. 6.13PCh. 6.9 - Predict the major products of the following...Ch. 6.9 - Prob. 6.15PCh. 6.10A - Prob. 6.16PCh. 6.11A - When diethyl ether (CH3CH2OCH2CH3) is treated with...Ch. 6.11B - Prob. 6.18PCh. 6.11B - For each pair of compounds, state which compound...Ch. 6.12 - Prob. 6.20PCh. 6.12 - Under appropriate conditions...Ch. 6.13 - Propose an SN1 mechanism for the solvolysis of...Ch. 6.13B - Prob. 6.23PCh. 6.13B - 3-Bromocyclohexene is a secondary halide, and...Ch. 6.15 - Prob. 6.25PCh. 6.15 - Prob. 6.26PCh. 6.16 - For each reaction, give the expected substitution...Ch. 6.16 - Prob. 6.28PCh. 6.16 - Prob. 6.29PCh. 6 - Prob. 6.30SPCh. 6 - Draw the structures of the following compounds. a....Ch. 6 - Give systematic (IUPAC) names for the following...Ch. 6 - Prob. 6.33SPCh. 6 - Predict the compound in each pair that will...Ch. 6 - Prob. 6.35SPCh. 6 - Give two syntheses for (CH3)2CHOCH2CH3, and...Ch. 6 - Prob. 6.37SPCh. 6 - Prob. 6.38SPCh. 6 - Chlorocyclohexane reacts with sodium cyanide...Ch. 6 - Give the substitution products expected from...Ch. 6 - Prob. 6.41SPCh. 6 - Prob. 6.42SPCh. 6 - Two of the carbocations in Problem6-42 are prone...Ch. 6 - Prob. 6.44SPCh. 6 - Predict the products of the following SN2...Ch. 6 - Prob. 6.46SPCh. 6 - Strawberry growers have used large quantities of...Ch. 6 - A solution of pure (S)-2-iodobutane ([]=+15.90) in...Ch. 6 - Prob. 6.49SPCh. 6 - Give a mechanism to explain the two products...Ch. 6 - Prob. 6.51SPCh. 6 - Because the SN1 reaction goes through a flat...Ch. 6 - Prob. 6.53SPCh. 6 - Furfuryl chloride can undergo substitution by both...Ch. 6 - Prob. 6.55SPCh. 6 - The following reaction takes place under...Ch. 6 - Propose mechanisms to account for the observed...Ch. 6 - Prob. 6.58SPCh. 6 - Prob. 6.59SP
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