O Chem 1 Final Exam 2 and 3

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which is a meso compound

(2R,3S)-2,3-dibromobutane

select the correct name of the following compound (CH3 on 3 wedge, CH3 on 4 dashed)

(3R,4S)-3,4-dimethlyheptane

Select the name of the following compound (Cl on 3 wedge)

(S)-3-chloro-6-ethyloctane

the highest priority group using the Cahn-Ingold-prelog R and S nomenclature is

--CH2OH

In the lowest energy conformation of the compound below, how many alkyl substituents are axial

0

How many tertiary (3) hydrogens and primary (1) carbons in the following alkane, respectively

1 and 7

Identify the most appropriate reason for the instability of axial isopropycyclohexane

1,3 diaxial interactions

Which of the following alkyl halides reacts the fastest in an Sn2 reaction

1-bromo-4methlypentane

select the name of the following compound (begins with Cl and 2 lines up on 3)

1-chloro-2,2-dimethylbutane

Which of the following alkyl halides reacts the fasted in an SN2 reaction

1-iodobutane

How many quaternary (4) carbons and secondary (2) hydrogens in the following alkane respectively

2 and 2

enantiomeric excess % (ee%) of (S)-2-iodobutane in a mixture is 50%, what is the Toal amount of (R)-2-iodobutane in the mixture

25%

In the lowest energy conformation of the compound below, how many alkyl substituents are equatorial

3

Select the name of the following compound

3-bromo-2,3-dimethylpentane

IUPAC name of the following alkane

4-ethyl-5-methlyoctane

Name a different alkane

4-isopropyl-2-methylheptane

Name of the alkane

4-tert-butyl-2-methylheptane

what is the common name of the following alkyl group

5 carbons, one pointed up, A sec-butyl

enantiomeric excess % (ee%) of (S)-2-iodobutane in a mixture is 20% what is the total amount of (S)-2-iodobutane in the mixture

60%

Enatiomeric excess % (ee%) of (S)-2-iodobutane in a mixture is 40%. what is the total amount of (S)-iodobutane in the mixture

70%

indicate the statement that is FALSE about meso compounds

A meso compound is chiral

Which of the following is a Lewis acid

AlCl3

the structures below are drawn using different conventions, how are the represented compounds related

Diasteromers

which line angle drawing best represents the Newman projection shown below

B, CH3 and Cl on wedge, H CH3 on dashed

select the product of the following reaction 1)NaBr 2)NaCn

B, CN on a wedge bond

Which of the following structures has a different configuration from the other three

B, all R groups are connected from the bottom, H on top

Which of the following compounds is a bridged bicycle

Bicyclo [2.2.1] heptane

Select the product of the following reaction

Br leaves, two step reaction, N3 is on other side

Select the arrangement of the alkanes in order of increasing boiling point

Branched 2 and 4 C's on the last one

given the structure of aspartame (Nutrasweet) below, the configuration of the indicated chiral centers are

C3 is R and C6 is S

Select the best leaving group

CF3SO3

Which of the following structures has a different configuration from the other three

CH2 is solo on bottom, I

in the lowest energy conformation of the compound below, which alkyl substituents is(are) axial

CH3

Which of the following structures is considered a gauche conformer

CH3 CH3 beside each other

Select the most acidic compound

CH3CF2COOH

Select the polar Protic solvents

CH3CN and DMF

Order of chemical species from least to most basic

CH3S- < CH3O < NH2-

The highest priority group using the Cahn-Ingold-prelog R and S nomenclature is

CO2H

identify the electrophilic atom in the following reaction CH3CH2CH2CH2Br + NaN3

Carbon

Which of the following compounds has the lowest heat of combustion (most stable)

Ch3 wedge and Ch3 striped across

rank the following compounds in order of decreasing acidity, putting the most acidic first

ClCH2CH2OH > CH3CH2OH > CH3CH2NH2

Polar aprotic solvents

DMSO and CH3CO2H

Which is the best representation for electron pushing arrows for an Sn2 reaction

D, Br bond breaks and OCH3 forms where Br broke off

Identify the cis stereoisomer from the following structures

D, Hydrogen on the bottom

the following diagram represents the boat conformation for cyclohexane. identify the most appropriate reason for the instability of boat conformation

Flagpole interactions

which of the statements below correctly describes the conformations of acyclic alkanes

Gauche conformations are generally higher in energy than anti conformations

Which of the following is NOT a Lewis acid

HBr4

Identify the conjugate base HCO2H + -NH2 --- HCO2- + NH3

HCO2-

Symbol for helium

He

Select the polar aprotic solvents

I, II, IV

Select the best leaving group

I-

Select the order of the leaving group ability, putting the best first

I- > Br- > Cl- > H2O

arrange the following butane conformations in the order of increasing energy (lowest to highest)

I<III<II<IV

which of the compounds are chiral

II and III

in the reaction of Cl2 with ethane and UV light, which of the following reactions would be a chain propagation event

II and IV

Which of the following is a tertiary alkyl halide

II, with F

in the reaction of Cl2 with ethane and UV light, which of the following reactions would be a chain termination event(s)

III

which of the following compounds has the lowest heat of combustion (most stable)

III

which of the following structures of 2,3-dimethylbutane is the highest energy conformer

III, all elements are near each other

Which of the following contains the secondary radical carbons

IV and II

Arrange the following butane conformations in the order of decreasing energy (highest to lowest)

IV<II<III<I

What is the Keq for the following equilibrium (pKa of amides 15 and amines 35)

K>1

The symbol for nitrogen is

N

Identify the trans stereoisomer from the following structures

NH2 dashed, NH2 wedge on same side

In the following reaction, identify the conjugate base NH3 + H- --- NH2- + H2

NH2-

which of the following compounds is the strongest base

NH2-

Name the alkane CH3CH2CH2CH2CH2CH2CH2CH2CH3

Nonane

Symbol for Oxygen

O

Which of the following compounds is a Lewis base

OH-

the following alkyl halide is best described as (Has I at the bottom)

Secondary

What is the hybridization of the positively charged carbon in (CH3)3C+

Sp2

What is the hybridization of the negatively charged carbon in (CH3)3C-

Sp3

in the reaction of Cl2 with ethane and UV light which of the following reactions would be a chain initiation event

V

provide an acceptable name for the following compound

bicycle[2.1.1]hexane

Which of the following compounds is a fused bicycle

bicycle[3.2.0]heptane

Highest melting point

big + sign

how do alkyl substituents stabilize a carbocationic center to which they are attached

both a and c

going from left to right in the periodic table, basicity ____ and nucleoephility ____

decreases and decreases

going from left to right in the periodic table, nucleophilicity _____ and leaving group ability ______

decreases and increases

How are the two compounds related (one OH on dashed, one OH on wedge)

diasteromers

select the change in the rate of formation of the product if the concentration of the iodide ion is increased by 4 and the alkyl chloride is halved

doubles

Indicate the statement that is true about enantiomers

enantiomers are mirror image molecules that are not superimposable

select the charge in the rate of formation of the product if the concentration of the iodide ion is increased by 8 and the alkyl chloride is halved

increase by a factor of 4

Identify the NUCELOPHILIC atom in the following reaction

nitrogen

which of the following compounds has only primary and secondary hydrogen atoms

pentane

select the charge in the rate of formation of the product if the concentration of the iodide ion is halved and the alkyl chloride is doubled

remains unchanged

the following alkyl hailed is best described as (Cl equatorial and CH3 axial)

tertiary

Which of the statements below correctly describes the chair conformations of trans-1-ethyl-4-methylcyclohexane

the lower energy chair conformation has both substituents equatorial

how do alkyl substituents destabilize a carbanionic center to which they are attached

through inductive donation of electron density to the carbanionic center


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