Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 6.13, Problem 6.22P
Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.
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Propose syntheses of the following compounds starting with benzene or toluene. Assume ortho and
isomers can be separated.
a.
b.
O₂N-
Cl
COOH
para
0. Propose syntheses to carry out each of the following conversions. Assume ortho and para isomers can
be separated
a.
Br
b.
COOH
CH3
NH₂
PABA
(active ingredient in some sunscreens)
H3C
H
C=C
CH3
H
m-chloroperoxybenzoic acid
CH2Cl2, rt
C-C--.
H3CH2CC
H
H3C CH3
Cl₂
H₂O
NaOH
H₂O
D.
S-
E.
CH3
H₂O₂, H₂O
It
CH₂O Na
+
CHI
F.
HI, H₂O
heat
G.
4
OH
CH3CHCH3 + ICH2CH3
1. NaH
(CH3)3COH
(CH3)3 COCHCH2CH3
2.
CH3
5. Show how the ether below could be prepared from toluene and any other necessary reagents. Show all
reagents and all intermediate structures.
H3C-
H3C-
CI
OCH2CH3
Chapter 6 Solutions
Organic Chemistry (9th Edition)
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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- Given the major organic product(s) of each of the following reactions. If none is predicted, write "N.R." [answer 61 a. b. H3C C. NO₂ CH3CH2CH2Cl AICI 3 1) NaOH CI 2) H3O+ NO₂ 1. SnCl2, H3O+ 2. NaOH 3arrow_forwardPlease correct answer and don't used hand raitingarrow_forwardTo answer the following questions, consider the reaction below: CH3 . CH3 OH a. The best reagents for accomplishing the above transformation are.... a. 1. OsO4, pyridine 2. NaHSO3, H₂O b. 1. Hg(OAc)2, H₂O 1. C. 2. NaBH4 RCO₂H, CH2Cl₂ 2. H₂O* d. 1. BH3, THF 2. H₂O₂, OH b. The alcohol product is classified as a: a. 1° alcohol b. 2° alcohol C. 3° alcohol d. 4° alcohol c. The conversion of an alcohol into an alkyl chloride by reaction with SOCI2 is an example of: a. b. ن نخنه C. d. an El process an Syl process an E2 process an Sy2 processarrow_forward
- Estimation of ash in food Questions: Q1: What does the word ash refer to? Q2: Mention the types of ash in food Q3: Mention the benefit of using a glass dryerarrow_forwardDraw structures corresponding to the names given a. m-fluoronitrobenzene b. p-bromoaniline c. o-chlorophenol d. 3,5-dimethylbenzoic acidarrow_forwardIllustrate the reaction mechanism the following reactionarrow_forward
- Propose a synthesis for the following compound using benzene or toluene and any other reagents necessary. Show all major intermediate compounds that would probably be isolated during the course of your synthesis. on. Harrow_forwardProvide correct IUPAC names for each of the following compounds. NOT a. b. C. 2003 H,N- CH3 NH2 CHarrow_forward. Consider the reaction below to answer the following questions. OH 1. NaH 2. CH3I, ether O-CH3 A. Write the complete stepwise mechanism for the reaction. Show all intermediate structures and all electron flow with arrows. B. Mechanistically, the Williamson ether synthesis outlined above is: ن نخنه a. an El process b. an SN1 process C. an E2 process d. an SN2 process C. Alternatively, cyclopentyl methyl ether may be synthesized from cyclopentene. synthesis of cyclopentyl methyl ether from cyclopentene. Outline aarrow_forward
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