Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 20, Problem 20.27P
Draw the products formed when each compound is treated with two equivalents of
a. b. c.
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Draw the product formed when each compound is treated with two equivalents of CH;CH,CH,CHgMgBr
followed by H,0.
OCH3
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b.
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Draw the products formed when each compound is treated with CH3CH2COCl, AlCl3.
Draw the products formed when phenol(C6H5OH) is treated with each reagent. Give an explanation.
a. HNO3, H2SO4
h. product in (a), then Sn, HCl
Chapter 20 Solutions
Organic Chemistry-Package(Custom)
Ch. 20 - Prob. 20.1PCh. 20 - Which carbonyl groups in the anticancer drug taxol...Ch. 20 - Prob. 20.3PCh. 20 - Prob. 20.4PCh. 20 - Problem 20.5 What aldehyde or ketone is needed to...Ch. 20 - Prob. 20.6PCh. 20 - Problem 20.7 Draw the products formed when is...Ch. 20 - Prob. 20.8PCh. 20 - Prob. 20.9PCh. 20 - Prob. 20.10P
Ch. 20 - Draw the structure of both an acid chloride and an...Ch. 20 - Problem 20.12 Draw the products formed from ...Ch. 20 - Prob. 20.13PCh. 20 - Prob. 20.14PCh. 20 - What product is formed when...Ch. 20 - Prob. 20.16PCh. 20 - Problem-20.16 Review the oxidation reactions using...Ch. 20 - Problem-20.17 Write the step(s) needed to convert ...Ch. 20 - Problem-20.18 Oct-1-yne reacts rapidly with ,...Ch. 20 - Draw the product formed when each organometallic...Ch. 20 - Draw the product of each reaction. a.c. b.d.Ch. 20 - Draw the products including stereochemistry of the...Ch. 20 - What Grignard reagent and carbonyl compound are...Ch. 20 - Problem 20.24 Linalool (the Chapter 9 opening...Ch. 20 - Problem 20.25 What Grignard reagent and carbonyl...Ch. 20 - Prob. 20.26PCh. 20 - Draw the products formed when each compound is...Ch. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organocuprate reagent is needed to convert...Ch. 20 - What reagent is needed to convert (CH3)2CHCH2CHO...Ch. 20 - Prob. 20.31PCh. 20 - What carboxylic acid formed from each alkyl halide...Ch. 20 - Prob. 20.33PCh. 20 - Prob. 20.34PCh. 20 - Problem 20.35 Synthesize each compound from...Ch. 20 - Prob. 20.36PCh. 20 - 20.37 Devise a synthesis of each alcohol from...Ch. 20 - 20.38 Draw the products formed when pentanal is...Ch. 20 - Prob. 20.39PCh. 20 - Draw the product formed when CH3CH2CH2MgBr is...Ch. 20 - Draw the product formed when (CH3CH2CH2CH2)2CuLi...Ch. 20 - The stereochemistry of the products of reduction...Ch. 20 - Prob. 20.43PCh. 20 - What reagent is needed to convert...Ch. 20 - What reagent is needed to convert...Ch. 20 - Draw the products or each reduction reaction. a....Ch. 20 - Prob. 20.47PCh. 20 - Draw all stereoisomers formed in each reaction. a....Ch. 20 - Prob. 20.49PCh. 20 - 20.46 Treatment of ketone A with ethynylithium...Ch. 20 - 20.47 Explain why metal hydride reduction gives an...Ch. 20 - Prob. 20.52PCh. 20 - 20.49 Identify the lettered compounds in the...Ch. 20 - Prob. 20.54PCh. 20 - Draw a stepwise mechanism for each reaction. a. b.Ch. 20 - Prob. 20.56PCh. 20 - 20.54 Draw a stepwise mechanism for the following...Ch. 20 - What Grignard reagent and aldehyde or ketone are...Ch. 20 - Prob. 20.59PCh. 20 - What ester and Grignard reagent are needed to...Ch. 20 - What organolithium reagent and carbonyl compound...Ch. 20 - 20.59 What epoxide and organometallic reagent are...Ch. 20 - Prob. 20.63PCh. 20 - 20.61 Propose two different methods to synthesize...Ch. 20 - Synthesize each compound from cyclohexanol using...Ch. 20 - Prob. 20.66PCh. 20 - Prob. 20.67PCh. 20 - Devise three different methods to prepare each...Ch. 20 - Convert benzene into each compound. You may also...Ch. 20 - Design a synthesis of each compound from alcohols...Ch. 20 - Synthesize each compound from the given starting...Ch. 20 - 20.69 An unknown compound A (molecular formula )...Ch. 20 - 20.70 Treatment of compound C (molecular formula )...Ch. 20 - 20.71 Treatment of compound E (molecular formula )...Ch. 20 - 20.72 Reaction of butanenitrile () with methyl...Ch. 20 - 20.73 Treatment of isobutene with forms a...Ch. 20 - Prob. 20.77PCh. 20 - Prob. 20.78PCh. 20 - 20.76 Lithium tri-sec-butylborohydride, also known...Ch. 20 - Prob. 20.80PCh. 20 - Prob. 20.81PCh. 20 - Prob. 20.82PCh. 20 - 20.80 Draw a stepwise mechanism for the following...Ch. 20 - Prob. 20.84P
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- Draw the products formed when each acetal is treated with aqueous acid.arrow_forwardDraw the products formed when phenol(C6H5OH) is treated with each reagent. Give an explanation. e. Br2, FeBr3 f. Br2arrow_forwardDraw the products formed when each ether is treated with two equivalents of HBr. a. (CH3),COCH,CH,CH3 b. С. FOCH3arrow_forward
- Draw the product formed when each compound is treated with two equivalents of CH3CH2CH2CH2MgBr followed by H2O.arrow_forwardDraw the products formed when each alkyl halide is treated with NaCN.arrow_forwardDraw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent.arrow_forward
- Compounds that contain both a hydroxyl group (OH) and a carboxyl group (COOH) can undergo an intramolecular esterifi cation reaction. What product is formed when each hydroxy acid undergoes an intramolecular reaction? a. HOCH 2CH 2CH 2CH 2CO 2H b. HOCH 2CH 2CH 2CO 2Harrow_forwardDraw the product formed when CH3CH2CH2CH2NH2 reacts with each carbonyl compound in the presence of mild acidarrow_forwardShow how to bring about each conversion in good yield. a. b. C6H5 Cl OH COOH C6H5 COOHarrow_forward
- Draw the products formed when each alkyl halide is treated with NaCN. а. b.arrow_forwardWhat product is formed when each compound is treated with either LiAlH4 (followed by H2O), or NaBH4 in CH3OH?arrow_forwardProvide all possible products formed in the given reaction Draw the products formed when each ether is treated with two equivalents of HBr.arrow_forward
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