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chemistry
organic chemistry

Questions and Answers of Organic Chemistry

Show the conjugate bases of these species:
Complete these acid-base equations. Use the curved arrow method to show the electron movement in the reactions.
Indicate whether each of these species is a Lewis acid, a Lewis base, or both:
Provide the values for the missing Ka or pKa in the following examples:(a) pKa = – 4; Ka =?(b) Ka = 1 x 10–16; p pKa =?(c) pKa = 38; Ka =?(d) Ka = 1 x 106; pKa =?
Indicate whether these compounds are weaker or stronger acids than water (the Ka for water is 1.8 x 10?16; the pKa is 15.74):
Indicate whether these species are weaker or stronger bases than hydroxide ion. The Ka is or pKa values are for the conjugate acids.
Using the information available in Figure 4.2, predict the position of the equilibrium in these reactions; that is, predict whether there is a higher concentration of reactants or products present at
Use the information in Figure 4.2 to predict the positions of the equilibria in the reactions in problem 4.4.
Draw diagrams like that in Figure 4.3 for the reactions in problem 4.9.
Show a free energy versus reaction progress diagram for the following reaction:
Which species is a stronger acid?
Which anion is the stronger base?
Which is the most acidic hydrogen in each of these compounds?(a) H2NCH2CH2OH(b) CH3CH2OH(c) CH3SH
Explain which compound is the stronger acid:(a) CHF2CO2HorCH2FCO2H(b) CHF2CO2HorCHBr2CO2H(c) CH3OCH2CO2HorCH3CO2H
Which is the most acidic hydrogen in CH3CH2C = CH?
Show the resonance structures for the conjugate base of the Meta isomer of nitro-phenol and confirm that the nitro group is less effective at stabilizing this anion than it is in the case of the Para
Explain which compound is a stronger acid:
Explain which compound is the weaker base.
Use Table 4.2 to predict whether the equilibrium for these reactions favors the reactants or the products.
Explain whether each of the following solvents would be acceptable for reactions involving this anion: (a) Liquid NH3 (b) CH3CH2OH (c)CH3CH2OCH2CH3
Show the conjugate acid of each of these species:
Show the most stable conjugate base of these compounds:
Which of these species can behave as a Lewis acid?
Which of these species can behave as a Lewis base?
Calculate the pKa for these compounds.
Calculate the Ka for these compounds.
Explain which compound is the stronger acid:
Explain which species is the stronger base:
Arrange these compounds in order of increasing acid strength:
Arrange these compounds in order of increasing base strength:
Arrange these compounds in order of increasing acid strength:
Use the tables in this chapter to predict whether these equilibria favor the reactants or the products:
Complete these equilibrium reaction sin the most reasonable manner possible using the curved arrow convention to show the movement of electrons in the reactions, Predict whether the reactants or the
Identify the most acidic hydrogen in each of these compounds:
Show the products of these acid-base reactions and predict whether the equilibria favor the reactants or the products:
Which compound is behaving as the Lewis acid and which as the Lewis base in this reaction?
Explain which of these compounds is the weaker base?
Explain why the proto-nation of an amide occurs at the O rather than the N.
Amino acids contain both a basic functional group, the amine, and an acidic functional group, the carboxylic acid. Thus, they can undergo an internal acid-base re-action as shown in the following
Di-peptides result from the reaction of two amino acids to form an amide. Explain which nitrogen of the following di-peptide is the stronger base:
Explain which nitrogen in the ring of the amino acid histidine is the stronger base:
The pKa of the carboxylic acid group of acetic acid is 4.7. The pKa of the carboxylic acid group of the conjugate acid of the amino acid alanine is 2.3. Explain the difference in these pKa values.
There are two isomeric conjugate acids that produce the following base. Show the structure of each and explain how they produce the same base upon loss of a proton.
When a is reacted with hydroxide ion, isomer b is formed. (a) Explain why b is favored over a at equilibrium. (b) Show the structure of the conjugate base of a and explain how this isomerization
Compound c is a slightly stronger acid than compound d. The CH3O group has both an inductive effect and a resonance effect on the acidity of d. (a) Explain how the inductive effect of the CH3O group
Explain why the pKa’s of compounds near the middle of Table 4.2 are often listed with two figures to the right of the decimal place (that is, for NH4+ the pKa = 9.24), whereas those at the
For each pair of compounds, explain which is the stronger acid?
Explain why the compound on the left is a stronger acid than the compound on the right.
Provide IUPAC name for these alkenes:
Draw the structures of these compounds:(a) 4-Methylocatane(b) 2, 4-Dimethyl-5 propyl decane
What is wrong with these names? Provide the correct name for each.(a) 5, 5 – Dimethyl-3-ethylhexane(b) 2-Dimethyl pentane
Provide name for these complex groups:
Name these compounds:
Draw structures for these compounds.(a) 4-(1-Methylethl) heptanes(b) 3-Ethyl-7-methyl-5-(1-methylpropyl) undecane
Designate each carbon of these compounds as primary, secondary, tertiary, or quaternary:
Name this compound using the common name for the group:
Draw the structure of 4-tert-butyl-2, 3-dimethyloctane.
Name the following compounds:
Draw structures for these compounds:(a) 1, 1-Dimethylcylohexane(b) Ethylcyclopropane
Name these compounds:
Draw structures for these compounds:(a) 3-Ethyl-3-hexene(b) Cyclobutene(c) 3-Propyl-cyclohexe-1,4-diene
Name these compounds:
Draw structures for these compounds:(a) 1-Pentyne(b) 2, 3, 4-Trimethyl-5-undecyne
Name these compounds:
Draw the structure of 3-bromo-4-butylcyclohexene.
Name these compounds:
Draw structures for these compounds.(a) 2-Methylcylohexanol(b) 4-Methyl-4-penten-2-ol
Name thesecompounds:
Name these compounds: (a) CH3CH2CH2NH2
Name these compounds:
Draw structures for these compounds:(a) Diethyl ammonium bromide(b) N-Methyl-3-(1-methylpropyl)-2-octanamine
Name thesecompounds:
Draw structures for these compounds:(a) 5-Ethyl-4-methylnonane(b) 2-Methyl-1, 3-hexadiene(c) 3-Methylcyclopentanol(d) 3-Octyne(e) sec-Butylcyclohexane(f) Tert-Butyl alcohol
Name the five isomers of C6H14.
Indicate whether each of the indicated carbons is primary, secondary, tertiary, or quaternary:
Draw compounds that meet these requirements:(a) A primary alcohol(b) A tertiary alcohol(c) A secondary alkyl chloride(d) A secondary amine
What is wrong with the name given for these compounds? Provide the correct name for each.
Name these compounds:
Draw structures for these compounds:(a) 1, 5-Dibromo-2, 2-dichloro-4-ethyl-4-methyl-3-hexanol(b) 2, 2, 5, 6-Tetramethylcyclohex-3-enol(c) tert-Butylamine(d) 1, 2-Cyclopentanediol(e) Dibutyl ether(f)
Menthol is a component of oil of peppermint. Label each carbon of menthol as primary, secondary, tertiary, or quaternary. Should menthol be classified as a primary, secondary, or tertiary alcohol?
Provide systematic name for these naturally occurring compounds:
The systematic name of the ? CH = CH2 group is ethenyl: Provide a systematic name for limonene, which is found in lemons and other citrus-fruits.
Vitamin A alcohol is 3, 7 dimethyl-9-(2, 6, 6-trimethyl-1-cyclohexenyl)-2, 4, 6, 8-nonatetraen-1-o1, Draw the stricter of vitamin A alcohol.
Explain which compound has the higher melting point:(a) Cyclopentane or pentane(b) 1-Pentanol or pentane
Explain which compound has the higher boiling point:(a) Octane or nonane(b) Nonane or 3-nonene(c) 1-Nonyne or 1-nonanol(d) Trim ethylamine or propylamine(e) Cyclopentanol or diethyl ether(f) 1-Butene
Chloroform, CHCl3, is a common solvent in the organic laboratory. It is not miscible with water, so a mixture of these two solvents forms two layers, which solvent do you expect to form the lower
Predict which of these compounds has the higher solubility in water:(a) 1-Butanol or 1-chlorobutane(b) 1-Butanol or 1-hexanol(c) Pentane or diethyl amine
While working in the chemical stockroom, you discover an unlabeled bottle containing a liquid compound. You carefully smell the liquid and discover that it has a fishy odor. What functional group do
Turpentine, obtained from pine trees, is composed primarily of ?-pinene and ?-pinene, Explain whether you expect turpentine to mix with water. If a point dissolves in turpentine, what does this
The structure of a typical fat is shown here. Estimate the energy content of fat compared to the other compounds discussed in the Focus On box on p. 146 and explain yourreasoning.
Name these compounds.
Explain which compound has the higher boiling point.
Explain which compound has the higher boiling point. Discuss.
Explain which compound has the higher solubility in water.
Which of these compounds exhibit cis-trans isomerism? Draw both cis-trans isomers when they exist?
Draw the cis-trans isomers for these compounds and explain which is more stable:
Which of these groups has the higher priority?
Assign these compounds as the Z or Eisomers:
Draw a plot of energy versus dihedral angle for the conformations of propane about one of the C-C bonds:
Draw a Newman projection of the highest-energy conformation of 2,3-dimethylbutane about the C2-C3 bond.

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