Which has a. the higher boiling point: 1-bromopentane or 1-bromohexane b. the higher

a. How many hydrogens does an alkane with 17 carbons have? b. How many carbons does an alkane with 74 hydrogens have?

Draw the structures of octane and isooctane.

Draw a condensed structure and a skeletal structure for each of the following compounds: a. sec -butyl tert -butyl ether e. 5-(1,2-dimethylpropyl)nonane i. 3-ethoxy-2-methylhexane b. isoheptyl alcohol f. triethylamine j. 5-(1,2-dimethylpropyl)nonane c. sec -butylamine g. 4-(1,1-dimethylethyl)heptane k. 3,4-dimethyloctane d. isopentyl bromide h. 5,5-dibromo-2-methyloctane l. 4-(1-methylethyl)nonane

List the following compounds from highest boiling to lowest boiling: OH NH2 O O OH

a. What is each compounds systematic name? b. Draw a skeletal structure for each condensed structure given, and draw a condensed structure for each skeletal structure given in the following list: 1. (CH 3 ) 3 CCH 2 CH 2 CH 2 CH(CH 3 ) 2 5. BrCH2CH2CH2CH2CH2NHCH2CH3 9. NCH3 CH3 2. Br 6. 10. OH CH2CH3 3. CH3CHCH2CHCH2CH3 CH3 OH 7. CH3CH2CHOCH2CH3 CH2CH2CH2CH3 11. CH3 Br 4. (CH 3 CH 2 ) 4 C 8. CH 3 OCH 2 CH 2 CH 2 OCH

Which of the following represents a cis isomer? CH3 CH3 CH3 CH3 CH3 CH3 CH3 CH3

a. How many primary carbons does each of the following compounds have? b. How many secondary carbons does each one have? c. How many tertiary carbons does each one have? 1. CH3 CH2CH3 CH2CHCH3

Which of the following conformers of isobutyl chloride is the most stable? Cl Cl Cl CH3 CH3 H3C CH3 CH3 H CH3 H H H H H

Draw the structural formula for an alkane that has a. six carbons, all secondary. b. eight carbons and only primary hydrogens. c. seven carbons with two isopropyl groups.

What is each compounds systematic name? a. CH3CH2CHCH3 NH2 e. CH3CHCH2CH2CH3 CH3 h. CH3CHCH2CH2CH2OH CH3 b. CH3CH2CHCH3 Cl f. CH3 CH3CHNH2 i. Br c. CH3CH2CHNHCH2CH3 CH3 g. CH2CH3 CH3C CH3 Br j. OH d. CH3CH2CH2OCH2CH3

Which has a. the higher boiling point: 1-bromopentane or 1-bromohexane? b. the higher boiling point: pentyl chloride or isopentyl chloride? c. the greater solubility in water: 1-butanol or 1-pentanol? d. the higher boiling point: 1-hexanol or 1-methoxypentane? e. the higher melting point: hexane or isohexane? f. the higher boiling point: 1-chloropentane or 1-pentanol? g. the higher boiling point: 1-bromopentane or 1-chloropentane? h. the higher boiling point: diethyl ether or butyl alcohol? i. the greater density: heptane or octane? j. the higher boiling point: isopentyl alcohol or isopentylamine? k. the higher boiling point: hexylamine or dipropylamine?

a. Draw Newman projections of the two conformers of cis -1,3-dimethylcyclohexane. b. Which of the conformers would predominate at equilibrium? c. Draw Newman projections of the two conformers of the trans isomer. d. Which of the conformers would predominate at equilibrium?

Ansaid and Motrin belong to the group of drugs known as nonsteroidal anti-infl ammatory drugs (NSAIDs). Both are only slightly soluble in water, but one is a little more soluble than the other. Which of the drugs has the greater solubility in water? CH3CHCH2 CHCOOH CH3 CH3 CHCOOH CH3

Draw a picture of the hydrogen bonding in methanol.

A student was given the structural formulas of several compounds and was asked to give them systematic names. How many did the student name correctly? Correct those that are misnamed. a. 4-bromo-3-pentanol e. 5-(2,2-dimethylethyl)nonane i. 1-bromo-4-pentanol b. 2,2-dimethyl-4-ethylheptane f. isopentyl bromide j. 3-isopropyloctane c. 5-methylcyclohexanol g. 3,3-dichlorooctane k. 2-methyl-2-isopropylheptane d. 1,1-dimethyl-2-cyclohexanol h. 5-ethyl-2-methylhexane l. 2-methyl- N , N -dimethyl-4-hexanamine

Which of the following conformers has the highest energy (is the least stable)? AB C CH3 Cl CH3

Give the systematic names for all alkanes with molecular formula C 7 H 16 that do not have any secondary hydrogens.

Draw skeletal structures for the following: a. 5-ethyl-2-methyloctane c. 2,3,3,4-tetramethylheptane e. 2-methyl-4-(1-methylethyl)octane b. 1,3-dimethylcyclohexane d. propylcyclopentane f. 2,6-dimethyl-4-(2-methylpropyl)decane

For rotation about the C@3 i C@4 bond of 2-methylhexane, do the following: a. Draw the Newman projection of the most stable conformer. b. Draw the Newman projection of the least stable conformer. c. About which other carboncarbon bonds may rotation occur? d. How many of the carboncarbon bonds in the compound have staggered conformers that are all equally stable?

Draw all the isomers that have molecular formula C 5 H 11 Br. ( Hint: There are eight.) a. Give the systematic name for each of the isomers. b. Give a common name for each isomer that has a common name. c. How many of the isomers are primary alkyl halides? d. How many of the isomers are secondary alkyl halides? e. How many of the isomers are tertiary alkyl halides?

What is each compounds systematic name?

Draw the two chair conformers for each of the following, and indicate which conformer is more stable: a. cis -1-ethyl-3-methylcyclohexane d. cis -1,2-diethylcyclohexane b. trans -1-ethyl-2-isopropylcyclohexane e. cis -1-ethyl-3-isopropylcyclohexane c. trans -1-ethyl-2-methylcyclohexane f. cis -1-ethyl-4-isopropylcyclohexane

Why are lower molecular weight alcohols more soluble in water than higher molecular weight alcohols

a. Draw a potential energy diagram for rotation about the Ci C bond of 1,2-dichloroethane through 360, starting with the least stable conformer. The anti conformer is 1.2 kcal/mol more stable than a gauche conformer. A gauche conformer has two energy barriers, 5.2 kcal/mol and 9.3 kcal/mole. b. Draw the conformer that would be present in greatest concentration. c. How much more stable is the most stable staggered conformer than the most stable eclipsed conformer? d. How much more stable is the most stable staggered conformer than the least stable eclipsed conformer?

For each of the following compounds, is the cis isomer or the trans isomer more stable?

For each of the following compounds, is the cis isomer or the trans isomer more stable?

Draw the most stable conformer of the following molecule. (A solid wedge points out of the plane of the paper toward the viewer. A hatched wedge points back from the plane of the paper away from the viewer.)

What is each compounds systematic name? a. CH3CH2CHCH2CH2CHCH3 NHCH3 CH3 c. CH3CHCHCH2Cl Cl CH2CH3 e. b. CH3CH2CHCH2CHCH2CH3 CH3CHCH3 CH3 d. CH3CHCH3 CH3CH2CHCH3

Calculate the energy difference between the two chair conformers of trans -1,2-dimethylcyclohexane.

The most stable form of glucose (blood sugar) is a six-membered ring in a chair conformation with its fi ve substituents all in equa torial positions. Draw the most stable conformer of glucose by putting the OH groups on the appropriate bonds in the structure on the right.

What is each compounds systematic name? Br CH3 CH3CHCH2CHCH2CH3 b. c. a. e. f. d. CH3 OH CH3CHCHCH2CH3 OH OH CH3CHCH2CH2CHCH2CH2CH3 g. CH3 Br OH OH HO h. Br B

Explain the following: a. 1-Hexanol has a higher boiling point than 3-hexanol. b. Diethyl ether has very limited solubility in water, but tetrahydrofuran is completely soluble.

One of the chair conformers of cis -1,3-dimethylcyclohexane is 5.4 kcal/mol (23 kJ/mol) less stable than the other. How much steric strain does a 1,3-diaxial interaction between two methyl groups introduce into the conformer?

Bromine is a larger atom than chlorine, but the equilibrium constants in Table 3.9 indicate that a chloro substituent has a greater preference for the equatorial position than a bromo substituent does. Suggest an explanation for this fact.

Name the following compounds:

Using the data obtained in Problem 78, calculate the percentage of molecules of trans -1,2-dimethylcyclohexane that will have both methyl groups in equatorial positions.

Using the data obtained in Problem 82, calculate the amount of steric strain in each of the chair conformers of 1,1,3-trimethylcyclohexane. Which conformer would predominate at equilibrium?