PROBLEM 1. Which of the isomeric C4H₁0O alcohols can be prepared by hydrogenation of aldehydes? Which can be prepared by hydrogenation of ketones? Which cannot be prepared by hydrogenation of a carbonyl compound? (Hint: Draw all the isomers of C4H10O alcohols and classify each as primary, secondary, or tertiary. From the classification you wil be able to answer the questions.)

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PROBLEM 1. Which of the isomeric C₂H₁0O alcohols
can be prepared by hydrogenation of aldehydes?
Which can be prepared by hydrogenation of ketones?
Which cannot be prepared by hydrogenation of a
carbonyl compound? (Hint: Draw all the isomers of
C4H10O alcohols and classify each as primary,
secondary, or tertiary. From the classification you will
be able to answer the questions.)
Problem 2. Each of the following alcohols has
been prepared by reaction of a Grignard reagent
with ethylene oxide. Select the appropriate
Grignard reagent in each case.
(a)
CH3
-CH₂CH₂OH
(b)
CH₂CH₂OH
Problem 3. Write equation showing how 3-
Methyl-1,5-pentanediol could be prepared from
a dicarboxylic acid.
Transcribed Image Text:PROBLEM 1. Which of the isomeric C₂H₁0O alcohols can be prepared by hydrogenation of aldehydes? Which can be prepared by hydrogenation of ketones? Which cannot be prepared by hydrogenation of a carbonyl compound? (Hint: Draw all the isomers of C4H10O alcohols and classify each as primary, secondary, or tertiary. From the classification you will be able to answer the questions.) Problem 2. Each of the following alcohols has been prepared by reaction of a Grignard reagent with ethylene oxide. Select the appropriate Grignard reagent in each case. (a) CH3 -CH₂CH₂OH (b) CH₂CH₂OH Problem 3. Write equation showing how 3- Methyl-1,5-pentanediol could be prepared from a dicarboxylic acid.
Problem 4. Write the structure of the ester
formed in each of the following reactions:
CHỊCH, CON
i
(a) CH₂CH₂CH₂CH₂OH + CH₂CH₂COH H₂SO4
heat
HOLLOH
Hoi
(b) 2CH3OH + HOC
-ČOH
H₂SO4
heat
Problem 5. Predict the principal organic product
of each of the following reactions:
K₂Cr₂O7
(a) CICH₂CH₂CH₂CH₂OH H₂SO4, H₂O
Na₂Cr₂O7
(b) CH,CHCH,CH,CH,CH,CH,CH3 H,SO%,H,O
H₂SO4, H₂O
ОН
(c)
CH3CH₂CH₂CH₂CH₂CH₂CH₂OH
PCC
CH₂Cl₂
Transcribed Image Text:Problem 4. Write the structure of the ester formed in each of the following reactions: CHỊCH, CON i (a) CH₂CH₂CH₂CH₂OH + CH₂CH₂COH H₂SO4 heat HOLLOH Hoi (b) 2CH3OH + HOC -ČOH H₂SO4 heat Problem 5. Predict the principal organic product of each of the following reactions: K₂Cr₂O7 (a) CICH₂CH₂CH₂CH₂OH H₂SO4, H₂O Na₂Cr₂O7 (b) CH,CHCH,CH,CH,CH,CH,CH3 H,SO%,H,O H₂SO4, H₂O ОН (c) CH3CH₂CH₂CH₂CH₂CH₂CH₂OH PCC CH₂Cl₂
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