Ch 20 Ochem

Ph3P=CHCH2CH2CH3
Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction.
H > phenyl > t-butyl > methyl
What is the correct order of migration rate for the following groups in the Baeyer-Villiger oxidation reaction?
oxirane
What is the correct order of migration rate for the following groups in the Baeyer-
Villiger oxidation reaction?
(CH3)3CO=CH
A compound with formula c5h10o shows two singlets, in the 1H NMR spectrum.
Which one of the following is a possible structure for this compound?
2,4-dimethyl-3-pentanone
The 1H NMR spectrum of a compound with formula c7h14o shows two signals. Which one of the following is a possible structure for this compound?
2,2-dimethyl-3-pentanone
The 13C NMR spectrum of a compound with formula C7H14O shows five signals. Which one of the following is a possible structure for this compound?
2-methylhexanal
The 1H NMR spectrum of a compound with formula C7H14O shows a doublet at 9.2 ppm. Which one of the following is a possible structure for this compound?
2-pentanone
Provide a structure for the compound with molecular formula C5H10O and with the following spectroscopic data.
IR: 1720 cm?1
1H NMR: 1.9? (triplet, I=3H), 1.7? (sextet, I=2H), 2.1? (singlet, I=3H), 2.4? (triplet, I=2H)
benzene ring with C=OCH2CH3
Provide a structure for the compound with molecular formula c9h10O and with the following spectroscopic data.
IR: 1680 cm?1
1H NMR: 1.25? (triplet, I=3H), 3.0? (quartet, I=2H), 7-8? (multiplet, I=5H)
1,2-dimethylcyclopentene
Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of compound A?
2-phenyl-2-pentene
Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?
3-methyloctanal
Predict the product for the following reaction.
3-methyl-1-octanol ?(PCC/CH2Cl2)
2-hexanone
Predict the product for the following reaction.
2-hexanol ?(PCC/CH2Cl2)
2-nitrobenzoic acid
Which one of the following is the strongest acid?
A) benzoic acid
B) 4-nitrobenzoic acid
C) 4-ethylbenzoic acid
D) 4-chlorobenzoic acid
E) 4-hydroxybenzoic acid
E
Fluorine is the most electronegative and is in the closest proximity of the carboxylic acid group. It will stabilize the conjugate base via an inductive effect, making it a weaker base.
Which one of the following is the strongest acid? Explain your choice.
A) 2,3-dimethylheptanoic acid
B) 3,3-dichlorohexanoic acid
C) 3-iodo-4-bromo-hexanoic acid
D) 3-chloro-4-bromoheptanoic acid
E) 2-fluoro-4-bromohexanoic acid
(CH3)2CuLi
Provide the reagents necessary to carry out the following conversion.
4-ethylheptanoyl chloride ? 5-ethyl-2-octanone
K2Cr2O7/H2SO4/H2O

SOCl2

(CH3CH2CH2)2CuLi

Provide the reagents necessary to carry out the following conversion.

5-phenyl-1-pentanol
? (1)
5-phenylpentanoic acid
?(2)
5-phenylpentanoyl chloride
?(3)
8-phenyl-4-octanone

tert-butyl acetate
A compound with molecular formula c6h12o2 exhibits two singlet in its 1HNMR spectrum, at ? 1.4 (I=9) and ? 2.0 (I=3). Its IR spectrum shows a strong absorption band near 1740 cm-1.
What is the structure for this compound?
ethyl acetoacetate
Which one of the following compounds is most acidic?
A) ethyl acetoacetate
B) 2-butanone
C) ethyl pentanoate
D) 1-butanol
E) 3-pentanone
sodium hydride
LDA
Which of the following base will completely convert 1,4-cyclohexanedione into an
enolate?
A) sodium hydroxide
B) sodium ethoxide
C) LDA
D) sodium hydride
2-pentanone
Which of the following ketones will give a positive iodoform test?
A) 3-heptanone
B) 3-hexanone
C) cyclohexanone
D) 2-pentanone
E) 2-methyl-3-hexanone
1. NaOH/Br2 2. H3O
Provide the reagents necessary to convert acetophenone to benzoic acid
2,2-dimethylbutanal
Which one of the following compound does not undergo an aldol addition reaction in presence of aqueous sodium hydroxide?
A) butanal
B) 2-methylbutanal
C) 3-methylpentanal
D) 2,2-dimethylbutanal
E) none of these
Use of CH3ONa will result in transesterification product.
Explain why CH3ONa should not be used for Claisen condensation of ethylbutanoate.

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