Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 6.16, Problem 6.27P
For each reaction, give the expected substitution product and predict whether the mechanism will be predominantly first order (SN1) or second order (SN2).
- a. 2 – chloro – 2 – methylbutane + CH3COOH
- b. isobutylbromide + sodiummethoxide
- c. l – iodo – 1 – methylcyclohexane + ethanol
- d. cyclohexylbromide + methanol
- e. cyclohexylbromide + sodiumethoxide
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3. Predict the major products for the following reactions. Indicate the type of mechanism observed (EAS,
NAS, or elimination-addition).
a.
b.
C.
NO₂
Br
Br
CI
NaOMe
heat
1. NaNH2, NH3
2. H3O+
NaNH2, NH3
Br
tBuO
H3C
H3C
CH2
H2
Alkyl halides undergo nucleophilic substitution and elimination reactions. When the kinetics of the reaction are
measured, if the rate of the reaction is found
alkyl halide the reaction is second order. The substitution reaction is thus termed SN2, and the elimination reaction is
be dependent upon the concentration of the nucleophile as well as the
termed E2. These reactions are bimolecular and take place in a single step. In the SN2 reaction, the nucleophile attacks
the a-carbon from the backside and displaces the leaving group with an inversion of configuration occurring at the
carbon. In the E2 elimination reaction, strong base removes an acidic hydrogen from the B-carbon and an alkene is
formed as the leaving group is expelled from the a-carbon. This elimination follows Zaitsev's rule whereby the more
substituted alkene is generally formed. In E2 elimination, both the B-hydrogen and the leaving group must be oriented
anti to each other.
The same reaction…
7. Reaction Scheme.
NH₂
NH2
or
two differnet methods
(no same steps/reagents)
C5H12N2
1. xs Mel,
xs K2CO3
2. Ag2O, H₂O
3. heat
Br2, xs NaOH,
xs H₂O
OHC
1.03
2. DMS
CHO
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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