ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260826791
Author: SMITH
Publisher: MCG
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Chapter 9.13, Problem 26P
Draw the product formed when
a.
b.
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Draw 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, imidazole
Draw 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, pyridine
Draw the organic product(s) formed when CH3CH2CH2OH is treated with each reagent.
a.H2SO4
b.NaH
c.HCl + ZnCl2
d.HBr
e.SOCl2, pyridine
f.PBr3
g.TsCl, pyridine
h. [1] NaH; [2] CH3CH2Br [1]
i.TsCl, pyridine; [2] NaSH
j.POCl3, pyridine
Chapter 9 Solutions
ORGANIC CHEMISTRY
Ch. 9.1 - Problem 9.1 Label each ether and alcohol in...Ch. 9.3 - Give the IUPAC name for each compound.Ch. 9.3 - Problem 9.3 Give the structure corresponding to...Ch. 9.3 - Name each of the following ethers.Ch. 9.3 - Name each epoxide.
a. (two ways) b. c. (two...Ch. 9.6 - Problem 9.8 Draw the organic product of each...Ch. 9.6 - Prob. 9PCh. 9.6 - Problem 9.10 Draw the products of each reaction.
...Ch. 9.8 - Problem 9.11 Draw the products formed when each...Ch. 9.8 - Prob. 12P
Ch. 9.11 - Problem 9.18 Draw the products of each reaction,...Ch. 9.11 - Problem 9.19 What is the major product formed...Ch. 9.12 - Prob. 19PCh. 9.12 - Prob. 20PCh. 9.12 - Problem 9.22 Draw the organic products formed in...Ch. 9.12 - Problem 9.23 Draw two steps to convert into each...Ch. 9.13 - Prob. 23PCh. 9.13 - Problem 9.25 Draw the products of each reaction,...Ch. 9.13 - Draw the products formed when (S)-butan-2-ol is...Ch. 9.13 - Draw the product formed when (CH3)2CHOH is treated...Ch. 9.14 - What alkyl halides are formed when each ether is...Ch. 9.14 - Explain why the treatment of anisole with HBr...Ch. 9.15 - Name each thiol.
a. b.
Ch. 9.15 - Draw the product of each reaction. ac b.d.Ch. 9.15 - Give the IUPAC name for each sulfide.
a. b.
Ch. 9.15 - Draw the product of each reaction.
a. b.
Ch. 9.16 - Prob. 33PCh. 9.16 - The cis and trans isomers of 2, 3-dimethyloxirane...Ch. 9.16 - Problem 9.36 Draw the product of each...Ch. 9 - 9.37 Name each compound depicted in the...Ch. 9 - Answer each question using the ball-and-stick...Ch. 9 - Prob. 38PCh. 9 - 9.40 Give IUPAC name for each...Ch. 9 - Prob. 40PCh. 9 - Prob. 41PCh. 9 - 9.46 What alkenes are formed when each alcohol is...Ch. 9 - Prob. 46PCh. 9 - Prob. 51PCh. 9 - 9.57 Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 53PCh. 9 - 9.59 Draw two different routes to each of the...Ch. 9 - Prob. 55PCh. 9 -
9.61 Draw the products formed when each ether is...Ch. 9 - 9.62 Draw a stepwise mechanism for each...Ch. 9 - Draw a stepwise, detailed mechanism for the...Ch. 9 - Prob. 59PCh. 9 - Draw the products of each reaction. a.c. b.d.Ch. 9 - Prob. 64PCh. 9 - Prob. 75P
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- Draw 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 of each reaction. CH3 a. CH3-C-CH,CH3 HCI HI OH HBr b. C. OHarrow_forwardDraw the product formed when (CH3)2CHOH is treated with each reagent (a, b and c)arrow_forward
- 4. What is the product of the following reaction? A. B. OH 1) CH3CH₂CH3MgBr 2) H₂O C. HO D.arrow_forwardReagents a. C6H5CHO b. NaOH, ethanol h. BrCH2CH=CH2 i. Na* OEt, ethanol j. Br2, H* k. K* t-BuO c. Pyrrolidine, cat. H* d. H2C=CHCN e. H3O* f. I. CH2(CO2ET)2 -CH2CH2CN LDA m. heat g. ELOC(=0)CO2ET Select reagents from the table to synthesize this compound from cyclopentanone. Enter the letters of the chosen reagents, in the order that you wish to use them, without spaces or punctuation (i.e. geda).arrow_forwardDraw the products formed when CH3CH2C=C Na+ reacts with each compound. a. CH3CH2CH2Br b.(CH3)2CHCH2CH2Cl c.(CH3CH2)3CCl d.BrCH2CH2CH2CH2OH e. ethylene oxide followed by H2O f.propene oxide followed by H2Oarrow_forward
- Draw the product formed when pentanal (CH3CH2CH2CH2CHO) is treated with each reagent. With some reagents, no reaction occurs.arrow_forwardClassify each alkyl halide as 1 °, 2 °, or 3 °.arrow_forward3. What product is formed when HO(CH₂) CHO is treated with each reagent? c. Ag₂O, NH OH d. Na₂Cr₂O₂, H₂SO4, H₂O a. NaBH, CH₂OH b. PCC 400arrow_forward
- Classify each alkyl halide as 1°, 2°, or 3°. CH3 c. CHg-C-CHCH3 ČH3 ČI CH;CH2CH,CH,CH2-Br b. d. a.arrow_forwardWhat is the major organic product obtained from the following reaction? A. CI B. H 1. (CH3CH₂)2CuLi 2. H3O+ C. D. •ay.a OHarrow_forwardDraw the products formed when D-altrose is treated with each reagent. a. (CH3)2CHOH, HCl b. NaBH4, CH3OH c. Br2, H2O d. HNO3, H2O e. [1] NH2OH; [2] (CH3CO)2O, NaOCOCH3; [3] NaOCH3 f. [1] NaCN, HCl; [2] H2, Pd-BaSO4; [3] H3O+ g. CH3I, Ag2O h. C6H5CH2NH2, mild H+arrow_forward
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