Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 11, Problem 11.21P
Use retrosynthetic analysis to show how
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Show how to synthesize carboxylic acids from oxidation of alcohols and aldehydes,carboxylation of Grignard reagents, oxidative cleavage of alkenes and alkynes,hydrolysis of nitriles, and oxidation of alkylbenzenes
Give the systematic (IUPAC) names for these molecules.
Boononon cnolonongron.
НаСНз
CHОССH2СH2СНCHЗ
CH3
phenyl propanoate
|4-methyl pentane methanoat
Incorrect.
You mixed up the acyl and
alkoxy portions of the
molecule.
Name the alkoxy part first,
followed by the acyl part.
4. Show the steps and reagents needed to transform 1-propyne into 2-methylheptane.
You may use any alkyl halide and inorganic reagents.
1-propyne →
2-methylheptane
Chapter 11 Solutions
Organic Chemistry
Ch. 11 - Problem 11.1 Neopheliosyne B is a novel acetylenic...Ch. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Draw additional resonance structures for each...Ch. 11 - Problem 11.9 Draw the products formed when is...Ch. 11 - Explain the following result. Although alkenes...
Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne.
a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
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- Show how to convert alkenes, alkyl halides, and carbonyl compounds to alcohols.arrow_forwardb) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forwardUpon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.arrow_forward
- True or False Considering that two carbon chains have equal number of carbons, but one has Fluorine and the other has Iodine, the one with iodine will have a higher boiling point. Mild oxidation of alkenes results to similar product as that of nucleophilic addition of water to aldehydes.arrow_forwardShow how norbornane can be prepared from cyclopentadiene.arrow_forwardProvide the product(s) for the reaction of benzene with nitric acid and sulfuric acid. If more than one product is formed, list the major product first. If no reaction, draw the starting material.arrow_forward
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