Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 6.16, Problem 6.28P
Interpretation Introduction
Interpretation: The enantiomeric excess and expected specific rotation for the expected product is to be calculated on the basis of given information.
Concept introduction: The concentration of the compound affects the rotation of polarized light in Polarimeter. The rotation is also dependent upon the length of the cell and optical activity of the compound. Optical purity of a compound is measured by the enantiomeric excess.
To determine: The enantiomeric excess and expected specific rotation for the expected product on the basis of given information.
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Students have asked these similar questions
When (S)-2-bromobutane undergoes an SN2 reaction with CH3O-, the product is
the compound shown below. What is/are the configuration(s) of the product(s)
obtained from this reaction?
O equal mixture of R and S
H₂C
a mixture of enantiomers with more R than S
S only
CH3
CH
OR only
O a mixture of enantiomers with more S than R
H₂
CH₂
Which characteristics describe an E2 reaction? Choose all that apply.
O Stereospecific
rate = k[E-LG]
Can form either the most substituted or least substituted alkene. It depends on the reagents used.
Always forms the most substituted alkene (Zaitzev's rule).
Unimolecular
O rate = k[base][E-LG]
Always forms the least substituted alkene (Hofmann's rule).
O Concerted
6. When optically pure (R)-2-bromobutane is heated with water, butan-2-ol
(CH3CHOHCH2CH3) is the product. The reaction forms twice as much (S)-butan-2-ol
as (R)-butan-2-ol. Calculate the ee and the specific rotation expected for the product.
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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