ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
9th Edition
ISBN: 9780137249442
Author: Wade
Publisher: INTER PEAR
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Textbook Question
Chapter 10, Problem 10.34SP
Predict which member of each pair is more acidic, and explain the reasons for your predictions.
- a. cyclopentanol or 3-chlorophenol
- b. cyclohexanol or cyclohexanethiol
- c. cyclohexanol or cyclohexanecarboxylic acid
- d. butan-1-ol or 2,2-dichlorobutan-1-ol
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1. Which is more acidic in each pair of compounds?
a. CH3CH2OH vs CF3CH2OH
b. Methanol vs 2-propanol
c. CH3CF2OH vs CH3CCI2OH
d. CH3CHFOH vs CH2FCH2OH
1. Rank each set of three alcohols in terms of increasing acidity, "1" being least acidic, and "3"
being most acidic.
goos
CCI3
CI3C.
Cl3
а.
ОН
ОН
OH
b.
OH
ОН
ОН
OH
С.
HO
Which is the more stable base? a. Br− or I− b. CH3O− or CH3S− c. CH3CH2O− or CH3COO− d. H2C CH or HC C− e. FCH2CH2COO− or CH2CH2COO- f. CLCH2CH2O- or CL2CHCH2O-
Chapter 10 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
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- 1. Draw the structure for each alcohol. a. 4,5-dimethyl-3-heptanol b. 4-methyl-2-hexanol c. 2-chloro-1-butanol 2. Draw the structure of the product for each reaction: a. OH K,Cr,0, H+ b. LOH Conc. H,SO4, 180°C Excess acidarrow_forwardWhich member of each pair is the stronger base? a. ethylamine or aniline b. ethylamine or ethoxide ion c. phenolate ion or ethoxide ion d. phenolate ion or acetate ionarrow_forwardWhich of the following is the most acidic compound? O d. 3,3,3-triiodopropanol All of the above are equivalent in term of their acidity . O C. 2,2,2-triflouropropanol O d. 22,2-tribromopropanol O e. 2,2,2-trichloropropanolarrow_forward
- Among the following, which is least acidic? a. p-nitrophenol b. o-cresol С. p-chlorophenol d. phenolarrow_forwardFor each compound, indicate the atom that is most apt to be protonated. a. CH3-CHOH-CH2NH2 b. CH3-C-NH2-CH3-OH c. CH3-C-CH3-NH2-CH2OHarrow_forwardPredict which member of each pair will be more acidic. Explain your answers. 2-chloropropan-1-ol or 3-chloropropan-1-olarrow_forward
- Draw the structure of a constitutional isomer of compound B that fits each description. a. an isomer that is at least 105 times more acidic than B b. an isomer that is at least 10 times less acidic than B c. an isomer that is comparable in acidity to B HO. Barrow_forwardWhich is a stronger base? a. HS− or HO− b. CH3O− or CH3NH c. CH3OH or CH3O d. Cl− or Br− e. CH3COO− or CF3COO− f. CH3CHClCOO− or CH3CHBrCOO−arrow_forwardAlkynes exhibit acidic properties because of the differences in the electronegativity of sp- hybridized carbons. Which of the following statements best explains the acidic property of acetylene? A. The electronegativity of sp hybridized carbon decreases bond dipole between C and H. B. Hydrogen atom becomes ionized due to sp-s repulsion. C. The sp-sp orbital overlap attracts the electron cloud between C and H. D. The pi bonds in the triple bond promote ionization of carbon into carbocationsarrow_forward
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