Organic Chemistry-Package(Custom)
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Author: SMITH
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Chapter 12, Problem 12.76P
Interpretation Introduction
Interpretation: Among the given alcohols, the one which gets oxidized rapidly by
Concept introduction: The oxidation by chromium ion favors the oxidation of sterically hindered alcohol as it leads to the relief of steric strain due to the transition from
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Which of the following alcohols will have NO REACTION upon oxidation with potassium dichromate in an acidic solution (Jones Oxidation)?
O 4-methyl-2-pentanol
O All of the given
O 2-methyl-2-pentanol
O 3-methyl-1-butanol
Many insects utilize cyclic ketal structures as pheromones such
as the structure shown below. The biosynthetic pathway
involves the cyclization of this acetal from the straight chain
structure. Draw the straight chain structure that could be used
to form this acetal. Use wedges and dashes to correctly depict
the stereochemistry.
H3C-
>
Substance
Substance A
Substance B
Substance C
Molecular Component
OH
OH
Substance
Substance D
Substance E
Molecular Component
Chapter 12 Solutions
Organic Chemistry-Package(Custom)
Ch. 12 - Prob. 12.1PCh. 12 - Prob. 12.2PCh. 12 - Prob. 12.3PCh. 12 - Prob. 12.4PCh. 12 - Prob. 12.5PCh. 12 - Given that syn addition of H2 occurs from both...Ch. 12 - Compound Molecular formula before...Ch. 12 - Draw the products formed when triacylglycerol A is...Ch. 12 - Prob. 12.9PCh. 12 - Prob. 12.10P
Ch. 12 - Problem 12.11 (a) Draw the structure of a compound...Ch. 12 - Prob. 12.12PCh. 12 - Prob. 12.13PCh. 12 - Prob. 12.14PCh. 12 - Prob. 12.15PCh. 12 - Prob. 12.16PCh. 12 - Prob. 12.17PCh. 12 - Problem 12.18 Draw the products formed when both...Ch. 12 - Prob. 12.19PCh. 12 - Prob. 12.20PCh. 12 - Prob. 12.21PCh. 12 - Prob. 12.22PCh. 12 - Prob. 12.23PCh. 12 - Problem 12.24 Draw the organic products in each of...Ch. 12 - Prob. 12.25PCh. 12 - Prob. 12.26PCh. 12 - Problem 12.27 Draw the products of each Sharpless...Ch. 12 - Prob. 12.28PCh. 12 - 12.29 Draw the products formed when A is treated...Ch. 12 - Prob. 12.30PCh. 12 - 12.31 Devise a synthesis of the following compound...Ch. 12 - Label each reaction as oxidation, reduction, or...Ch. 12 - Prob. 12.33PCh. 12 - Prob. 12.34PCh. 12 - Prob. 12.35PCh. 12 - Prob. 12.36PCh. 12 - 12.37 Stearidonic acid (C18H28O2) is an...Ch. 12 - Draw the organic products formed when cyclopentene...Ch. 12 - Prob. 12.39PCh. 12 - Draw the organic products formed when allylic...Ch. 12 - Draw the organic products formed in each reaction...Ch. 12 - Draw the organic products formed in each reaction....Ch. 12 - Prob. 12.43PCh. 12 - Prob. 12.44PCh. 12 - Prob. 12.45PCh. 12 - What alkene is needed to synthesize each 1,2-diol...Ch. 12 - Prob. 12.47PCh. 12 - Draw the products formed after Steps 1 and 2 in...Ch. 12 - Prob. 12.49PCh. 12 - Prob. 12.50PCh. 12 - Prob. 12.51PCh. 12 - What alkyne gives each set of products after...Ch. 12 - Prob. 12.53PCh. 12 - Prob. 12.54PCh. 12 - Prob. 12.55PCh. 12 - 12.54 An unknown compound A of molecular formula ...Ch. 12 - 12.55 DHA is a fatty acid derived from fish oil...Ch. 12 - Prob. 12.58PCh. 12 - Prob. 12.59PCh. 12 - 12.58 Epoxidation of the following allylic alcohol...Ch. 12 - What allylic alcohol and DET isomer are needed to...Ch. 12 - Devise a synthesis of each hydrocarbon from...Ch. 12 - Prob. 12.63PCh. 12 - 12.62 It is sometimes necessary to isomerize a cis...Ch. 12 - Prob. 12.65PCh. 12 - Prob. 12.66PCh. 12 - Prob. 12.67PCh. 12 - Prob. 12.68PCh. 12 - Devise a synthesis of each compound from the...Ch. 12 - Devise a synthesis of each compound from acetylene...Ch. 12 - Prob. 12.71PCh. 12 - Prob. 12.72PCh. 12 - Prob. 12.73PCh. 12 - Prob. 12.74PCh. 12 - Prob. 12.75PCh. 12 - Prob. 12.76PCh. 12 - 12.72 Draw a stepwise mechanism for the following...Ch. 12 - Prob. 12.78PCh. 12 - Prob. 12.79PCh. 12 - Prob. 12.80PCh. 12 - 12.75 Sharpless epoxidation of allylic alcohol X...
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- Identify the most important aldehyde and ketone from Section 14.4 on the basis of amount used, and list at least one characteristic for each that contributes to its usefulness.arrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward17-60 1-Propanol can be prepared by the reduction of an aldehyde, but it cannot be prepared by the acid catalyzed hydration of an alkene. Explain why it cannot be prepared from an alkene.arrow_forward
- Arrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forwardWhat structural and/or molecular properties of alcohols contributes to their reactivity with oxidizing reagent?arrow_forwardWhat is/are the product(s) when 2-methylhpentan-2-ol undergoes mild oxidation?arrow_forward
- Oxidation of aldehyde results in carboxylic aciid in a reaction similar to this: Draw the chemicals that form when the following chemicals are oxidized: a) 3-Chloropropanal b) methanalarrow_forwardWhat reducing agent can selectively reduce aldehydes, but not esters? KMnO4 OsO4 LiAlH4 NaBH4 What kind of compound is made when an aldehyde is treated with a Grignard reagent? Carboxylic acid Primary alcohol Secondary alcohol Tertiary alcoholarrow_forwardWhich of the following alcohols will be oxidized by potassium permanganate to form an aldehyde and then a carboxylic acid? OH H3C-CH₂-CH-CH₂-CH3 H3C-CH₂-CH₂-CH₂-CH₂-CH₂-OH OH CH3 H₂C-CH-CH-CH₂ CH3 OH H3C-CH-CH₂-CH₂-CH-CH3arrow_forward
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