Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 6.2, Problem 6.2P
Give the structures of the following compounds.
- a. methylene iodide
- b. carbon tetrabromide
- c. 3-bromo-2-methylpentane
- d. iodoform
- e. 2-bromo-3-ethyl-2-methylhexane
- f. isobutyl bromide
- g. cis-1-fluoro-3-(fluoromethyl)cyclohexene
- h. tert-butyl chloride
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Draw the skeletal structures for the compounds in
a. (Z)-1,3,5-tribromo-2-pentene b. (Z)-3-methyl-2-heptenec. (E)-1,2-dibromo-3-isopropyl-2-hexene d. vinyl bromidee. 1,2-dimethylcyclopentene f. diallylamine
Write the equation for the following
reactions:
a. 2-butene + HCI
b. 1,2-dichloro-1-propene + water
c. Propyne + oxygen
d. 1, 3-pentadiene + bromine
e.
cis-3,3,4-trimethyl-1-hexene + H₂ p
18. Which carbanion is the most stable
A. methyl carbanion (CH3-)
B. ethyl carbanion (CH3CH2-)
C. isopropyl carbanion ((CH3)2CH-)
D.Chloromethyl carbanion (CICH2-)
19. Which structural effect best explains the observed trend below:
Compound C-CI bond length (A)
1.78
1.77
1.76
H3C-CI
CIH₂C-CI
Cl₂HC-CI
FH₂C-CI
1.76
A. resonance B. C-H hyperconjugation C. Inductive effect D. steric effect
20. Assuming that each methyl/hydrogen 1,3-diaxial interaction destabilizes the
methyl substituted cyclohexane by 0.9 kcal/mole; then what is the energy
difference between 2 chair conformations of cis-1,3-dimethylcyclohexane.
A. 0.9 kcal/mol
B. 1.8 kcal/mol
C. 2.7 kcal/mol
D. 3.6 kcal/mol
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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