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Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 20, Problem 20.20P
Draw the product formed when each organometallic reagent is treated with
a. b.
d.
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Students have asked these similar questions
Draw the products formed in each reaction.
3. Draw the products formed when each compound is treated with HNO3 and H2SO4. State whether
the reaction occurs faster or slower than a similar reaction with be nzene.
COCH3
CN
OH
.CI
CH,CH3
a.
b.
C.
d.
e.
Draw the products of each reaction.
CH3
a. CH3-C-CH,CH3
HCI
HI
OH
HBr
b.
C.
OH
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 compound is treated with HNO3 and H2SO4.arrow_forward5. What reagents are needed to convert toluene (C,H,CH,) to each compound? a. C.H.COOH b. C.H₂CH₂Br c. p-bromotoluene d. o-nitrotoluene e. p-ethyltoluene f.arrow_forwardDraw the products formed when phenol (C6H5OH) is treated with each set of reagents. a. [1] HNO3, H2SO4; [2] Sn, HCl b. [1] (CH3CH2)2CHCOCl, AlCl3; [2] Zn(Hg), HCl c. [1] CH3CH2Cl, AlCl3; [2] Br2, hν d. [1] (CH3)2CHCl, AlCl3; [2] KMnO4arrow_forward
- Draw the organic product(s) formed when CH3CH₂CH₂OH is treated with each reagent. a. H₂SO4 d. HBr g. TsCl, pyridine b. NaH h. [1] NaH; [2] CH₂CH₂Br e. SOCI₂, pyridine f. PBr3 c. HCI + ZnCl₂ Hint: NaH deprotonates the alcohol forming an alkoxidearrow_forwardWhat alkenes are formed when each alcohol is dehydrated with TSOH? Label the major product when a mixture results. OH Xom OH a. OH b. CH₂CH3 OH C. d. CH₂CH₂CH₂CH₂OH e.arrow_forwardDraw the product formed when (CH3)2CHOH is treated with each reagent. a. SOCl2, pyridine b. TsCl, pyridine c. H2SO4 d. HBr e. PBr3, then NaCN f. POCl3, pyridinearrow_forward
- Draw the products formed from LiAlH4 reduction of each compound.arrow_forwardDraw the product formed when each organometallic reagent is treated with H2O.arrow_forwardDraw the products formed when each compound is treated with HNO3 and H2SO4.State whether the reaction occurs faster or slower than a similar reaction with benzene.arrow_forward
- Identify each compound as an ether, hemiacetal, or acetal.arrow_forwardWhat Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.arrow_forwardDraw the products formed when each dihalide is treated with excess NaNH2.arrow_forward
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