Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 8.1, Problem 1P
Label the
a.
b.
c.
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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 alkoxide
Draw the products formed when phenol(C6H5OH) is treated with each reagent. Give an explanation.
c. CH3CH2Cl, AlCl3
l. product in (c), then KMnO4
Draw the products formed when phenol(C6H5OH) is treated with each reagent. Give an explanation.
d. (CH3CH2)2CHCOCl, AlCl3
j. product in (d), then NH2NH2, –
OH
Chapter 8 Solutions
Organic Chemistry (6th Edition)
Ch. 8.1 - Problem 8.1 Label the and carbons in each alkyl...Ch. 8.2 - Problem 8.2 Classify each alkene in the following...Ch. 8.2 - Prob. 3PCh. 8.2 - Prob. 4PCh. 8.2 - Problem 8.5 Label each pair of alkenes as...Ch. 8.2 - Problem 8.6 Which alkene in each pair is more...Ch. 8.2 - Problem 8.7 Several factors can affect alkene...Ch. 8.4 - Prob. 8PCh. 8.4 - Prob. 9PCh. 8.4 - Prob. 10P
Ch. 8.4 - Prob. 11PCh. 8.5 - Problem 8.12 What alkenes are formed from each...Ch. 8.6 - Prob. 13PCh. 8.6 - Problem 8.14 What alkenes are formed from each...Ch. 8.6 - Problem 8.15 How does each of the following...Ch. 8 - 8.24 Rank the alkenes shown in the ball-and-stick...Ch. 8 - Prob. 25PCh. 8 - 8.26 What is the major E2 elimination product...Ch. 8 - Prob. 27PCh. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - 8.30 Label each pair of alkenes as constitutional...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - For each of the following alkenes, draw the...Ch. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - What alkene is the major product formed from each...Ch. 8 - Prob. 39PCh. 8 - Prob. 41PCh. 8 - Draw the products formed when each dihalide is...Ch. 8 - Draw all of the substitution and elimination...Ch. 8 - Prob. 56PCh. 8 - 8.59 Draw a stepwise, detailed mechanism for each...Ch. 8 - Draw the major product formed when...Ch. 8 - Draw a stepwise, detailed mechanism for the...Ch. 8 - Explain why the reaction of with gives ...Ch. 8 - Draw a stepwise detailed mechanism that...Ch. 8 - Prob. 63PCh. 8 - 8.65 Explain the selectivity observed in the...Ch. 8 - Prob. 65PCh. 8 - Prob. 66PCh. 8 - 8.68 (a) Draw all products formed by treatment of...
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- Draw the products formed when each alkene is treated with Grubbs catalystarrow_forwardDraw the product formed when pentanal (CH3 CH₂ CH₂ CH₂ CHO) is treated with each reagent. With some reagents, no reaction occurs. a. NaBH4, CH3OH b. [1] LiAiH4: [2] H₂O c. H₂, Pd-C d. PCC e. Na₂Cr₂O7, H₂SO4, H₂O f. Ag₂O, NH4OH g. [1] CH3 MgBr; [2] H₂O h. [1] C6H5 Li: [2] H₂O i. [1] (CH3)2 CuLi; [2] H₂O J. [1] HC=CNa; [2] H₂O k. [1] CH 3 C=CLI; [2] H₂O 1. The product in (a), then TBDMS-CI, imidazolearrow_forwardDraw the products formed when each compound is treated with CH;CH,COCI, AICI3. CH(CH3)2 N(CH)2 Br CH3 CH(CH)2 a. b. C. d. е.arrow_forward
- Draw the products (including stereoisomers) formed when benzaldehyde (C6H5CHO) is treated with each Wittig reagent.arrow_forwardWhich of the following are a. hemiacetals? b. acetals? c. hydrates?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
- 5. 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_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 product formed when pentanal (CH;CH,CH2CH;CHO) is treated with each reagent. With some reagents, no reaction occurs. a. NaBH4, CH,OH b. [1] LIAIH4; (2] H20 c. H2, Pd-C d. PCC e. NazCr,07, H2SO4, H2O f. Ag,0, NH,OH g. [1) CH,MgBr; (2] H2O h. [1] CęH,Li; [2] H20 i. [1] (CH3),CuLi; (2] H2O j. [1] HC=CNa; [2] H2O k. [1] CH;C=CLi; [2] H2O I. The product in (a), then TBDMS-CI, imidazolearrow_forward
- What alkenes are formed when each alcohol is dehydrated with TsOH? Label the major product when a mixture results.arrow_forwardDraw the products formed when each alcohol is dehydrated with H 2SO 4. Use the Zaitsev rule to predict the major product when a mixture forms.arrow_forwardIdentify each compound as an ether, hemiacetal, or acetal.arrow_forward
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