Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 10, Problem 10.39SP
Show how you would use Grignard syntheses to prepare the following alcohols from the indicated starting materials and any other necessary reagents.
- a. octan-3-ol from hexanal, CH3(CH2)4CHO
- b. octan-1-ol from 1-bromoheptane
- c. 1-cyclohexylethanol from acetaldehyde, CH3CHO
- d. 2-cyclohexylethanol from bromocyclohexane
- e. benzyl alcohol (Ph—CH2—OH) from bromobenzene (Ph—Br)
- f. cyclopentylphenylmethanol from benzaldehyde (Ph—CHO)
- g. octan-1-ol from 1-bromohexane
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Students have asked these similar questions
5. Show how the following alcohol can be synthesized.
a) 2-methyl butanol from suitable Grignard reagent
b) cyclohexanol from chlorocyclohexane
c) cylopentanol from cyclopentene
Specify both the alcohol starting material and the reagents you would use in each step in a synthesis of the compound shown. If the synthesis requires only two steps enter
"none" for step 3.
OH
Alcohol Starting Materials
1. methanol
2. ethanol
3. 1-propanol
4. 2-propanol
5. cyclohexanol
a. LiAlH4 f. PBr3
b. H₂SO4
c. HCI
d. HBr
e. SOC1₂
Reagents available
g. CrO3, H₂SO4, H₂O
h. NaH
i. CH3 MgBr; then H3O+
j. CH3 CH₂ MgBr; then H3O+
k. CH3 CH₂ CH₂ MgBr; then H3O+
I. C6H5 MgBr (phenylmagnesium bromide); then H3O+
m. (CH3)2 CHMgBr: then H3O+
n. Dess-Martin periodinane (DMP)
Write the number/letters of the alchol/reagents in the boxes below.
Alcohol starting material 4
Reagent for step 1 n
Reagent for step 2 j
Reagent for step 3 c
2. Using a Grignard reagent of your own choosing, how would you prepare the
following alcohols?
a. 2-methylpropan-2-ol
b. 1-Phenylethanol
c. 1-ethylcyclobutanol
CH 3
CH 3
-С —он
CHOH
Он
CH 3
Chapter 10 Solutions
Organic Chemistry (9th Edition)
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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