Organic Chemistry - With Access (Custom)
4th Edition
ISBN: 9781259147760
Author: OHIO UNIV.
Publisher: MCG
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Textbook Question
Chapter 20, Problem 20.22P
Draw the products (including stereochemistry) of the following reactions.
a. b.
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Chapter 20 Solutions
Organic Chemistry - With Access (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 product(s) formed when A is treated with each reagent.a. NaBH4, CH3OH b. LiAlH4, then H2O c. Ag2O, NH4OH d. CrO3, H2SO4, H2O e. PCCarrow_forwardb. a. C. HO Draw the products of each reaction. COOH COOH + NaOCH3 OH OH H₂SO4 H₂SO4arrow_forward16.41 Draw the products of each reaction. а. HNO3 H2SO4 'NO2 HO b. AICI3 CI С. H. Br2 FeBr3arrow_forward
- What is the structure of the product formed when A is heated in the presence of maleic acid? Explain why only one product is formed even though A has four double bonds. HOOC COOH A maleic acidarrow_forwardWhich of the following molecules contain a? good leaving group Which of the following molecules contain a good leaving group? он a. b. C. d. OHarrow_forwardDraw the structure and include stereochemistryarrow_forward
- Compound that is most easily hydrolyzed by acid in water `NH A. В. F C. D.arrow_forward16.41 Draw the products of each reaction. a. b. HO NO₂ mellanrios H HNO3 H₂SO4 Br₂ FeBr3 AICI3 d. e. Br- edmun adtonie F prier f. F (X) napoln NO₂ Cl₂ FeCl3 SO3 H₂SO4 onho sur + Na Sarrow_forward16.69 Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compaund. You may use benzene, acetylene (HC=CH), ethanol, ethylene oxide, and any inorganic reagents. a. b. CI он C ON d. NO2arrow_forward
- Suppose you have a mixture of these three compounds. Devise a chemical procedure based on their relative acidity or basicity to separate and isolate each in pure form.arrow_forwardDraw the product formed when A is treated with each series of reagents.a. [1] H2O; [2] NaH; [3] CH3Brb. [1] CuCN; [2] DIBAL-H; [3] H2O c. [1] C6H5NH2; [2] CH3COClarrow_forwardDraw the products formed when A or B is treated with each reagent. In some cases, no reaction occurs.a. NaBH4, CH3OHb. [1] LiAlH4; [2] H2Oc. [1] CH3MgBr (excess); [2] H2Od. [1] C6H5Li (excess); [2] H2Oe. Na2Cr2O7, H2SO4, H2Oarrow_forward
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