Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 5.7, Problem 5.13P
Interpretation Introduction
Interpretation: The percentage of (+)-butan-2-ol and (
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 percentage of (+)-butan-2-ol and (
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be
useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide.
QA O
• Use the wedge/hash bond tools to indicate stereochemistry where it exists.
• Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds.
• If enantiomers are formed, draw both.
• Separate multiple products using the + sign from the drop-down menu.
P
aste
ChemDoodleⓇ
▼ []
Previous Next
When 2-bromo-2-methylbutane is treated with a base, a mixture of 2-methyl-2-butene and 2-methyl-1-
butene is produced. When potassium hydroxide is the base, 2-methyl-1-butene accounts for 45% of the
product mixture. However, when potassium tert-butoxide is the base, 2-methyl-1-butene accounts for
70% of the product mixture. What percent of 2-methyl-1-butene would be in the mixture if potassium
propoxide were the base?
base
Br
A.
Less than 45%
B.
C.
45%
Between 45% and 70%
D.
More than 70%
Explain how the reaction of (CH3)2CHCH(Cl)CH3 with H2O yields two substitutionproducts, (CH3)2CHCH(OH)CH3 and (CH3)2C(OH)CH2CH3
Chapter 5 Solutions
Organic Chemistry (9th Edition)
Ch. 5.2 - Determine whether the following objects are chiral...Ch. 5.2A - Prob. 5.2PCh. 5.2B - Prob. 5.3PCh. 5.2B - Prob. 5.4PCh. 5.2C - Prob. 5.5PCh. 5.3 - Prob. 5.6PCh. 5.3 - Prob. 5.7PCh. 5.4D - Prob. 5.8PCh. 5.4D - Prob. 5.9PCh. 5.4D - Prob. 5.10P
Ch. 5.5 - Prob. 5.11PCh. 5.7 - When optically pure (R)-2-bromobutane is heated...Ch. 5.7 - Prob. 5.13PCh. 5.8 - Prob. 5.14PCh. 5.9B - Draw three-dimensional representations of the...Ch. 5.10A - For each sot of examples, make a model of the...Ch. 5.10A - Draw a Fischer projection for each compound....Ch. 5.10B - Prob. 5.18PCh. 5.10C - For each Fischer projection, label each asymmetric...Ch. 5.11C - Prob. 5.20PCh. 5.13 - Prob. 5.21PCh. 5.13 - Prob. 5.22PCh. 5.15 - Prob. 5.23PCh. 5.16A - Prob. 5.24PCh. 5 - The following four structures are naturally...Ch. 5 - For each structure, 1. star () any asymmetric...Ch. 5 - Prob. 5.27SPCh. 5 - Prob. 5.28SPCh. 5 - Prob. 5.29SPCh. 5 - Prob. 5.30SPCh. 5 - Prob. 5.31SPCh. 5 - Prob. 5.32SPCh. 5 - Prob. 5.33SPCh. 5 - Prob. 5.34SPCh. 5 - For each structure, 1. draw all the stereoisomers....Ch. 5 - Prob. 5.36SPCh. 5 - Prob. 5.37SPCh. 5 - 3,4-Dimethylpent-1-ene has the formula...Ch. 5 - A graduate student was studying enzymatic...Ch. 5 - Prob. 5.40SPCh. 5 - Prob. 5.41SP
Knowledge Booster
Similar questions
- A chemist synthesized compound X as a racemic mixture. When the ketone group in X was enzymatically reduced to the corresponding alcohol, a 100% yield was obtained of the product shown below. Choose the statement that best describes this result. ОН enzyme C;H1 `OCH,CH; pH 4.0 C3H1 `OCH,CH3 ОН ÕH X (racemic) (100% yield) One enantiomer of compound X reacts quickly with the enzyme. The other enantiomer of compound X is unreactive, but rapidly equilibrates with the reactive enantiomer under the reaction conditions. Since compound X was racemic, it makes sense that only a single product was obtained. O The product is a meso compound, so either enantiomer of compound X gives the same product. One enantiomer of compound X reacts quickly with the enzyme, while the other enantiomer of compound X remains unchanged.arrow_forwardThe synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. Aa • Use the wedge/hash bond tools to indicate stereochemistry where it exists. Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. If enantiomers are formed, draw both. Separate multiple products using the sign from the drop-down menu. .arrow_forwardfor question 25, Why is the answer B vs other options? Thank youarrow_forward
- МЕСНANISMS 1,2-epoxy-1-methylcyclopentane undergoes both acid-catalyzed and base-catalyzed opening of the epoxide ring to form two different products. > Using ethanol as the solvent and an appropriate acid, show the steps in the acid catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). > Using ethanol as the solvent and an appropriate base, show the steps in the base- catalyzed mechanism, writing structures for all products of the steps. Circle the major product(s). 1,2-epoxy-1-methylcyclopentane CH3arrow_forwardFor compound, indicate which group on the ring is more strongly activating and then draw a structural formula of the major product formed by nitration of the compound.arrow_forward2. Draw the structures of the products that would result from the following reactions. Ph Ph. (a) (c) Ph Ph co is also produced. Ph Ph (b) =0 + Ph-C=C-Ph → (d) Ph 10 Ph co is also produced. Benzyne adds to the 9, 10 position on anthracene.arrow_forward
- Nonearrow_forwardUsing Friedel Crafts alkylation of benzene, a group of scientists discovered compound A, C3H3O, an optically inactive compound. They discovered that compound B, CsH;BrO, is produced during the halogenation process. When compound B is reacted with nitric acid, compound C, C3H,B1NO3, is formed. While Friedel Crafts alkylation of compound A produces compound D. This compound D was oxidised to produce compound E, C9H§O3 as a major product. Compound F, C10H1002, was produced by Friedel Crafts acylation of compound A. This compound F reacts positively with alkaline iodine and 2,4- dinitrophenylhydrazine. However, it returns negative results for Tollens' and Benedict's tests. Identify the possible structural formulae compounds A to F and explain your answers.arrow_forwardSolve question 4arrow_forward
- 2²organic chemistry question answer with explanationarrow_forwardFollowing compounds are given to you:2-Bromopentane, 2-Bromo-2-methylbutane, 1-Bromopentane(i) Write the compound which is most reactive towards SN2 reaction.(ii) Write the compound which is optically active.(iii) Write the compound which is most reactive towards β – elimination reactionarrow_forwardExplain in detail the mechanism of how benzoic acid is converted to m-Nitrobenzyl alcohol. Use the picture as a reference.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
