Exam 3 O chem

Name the structure. clch2ch2 single down c single down h c double to c with line down to h line up to c with line up h c double c with line up ch3 line down h

(2E..........................4Z)......................7................chloro................2................4.....................hepta.....................diene

Name the structure. is it e or z saw horse with ch3 top left ch3ch2 bottom left ch2ch2ch2oh on top right and ch3 bottom right

(E).....................4...................5....................di...............methyl.................4................hepten..................1..............o.............l

Provide the systematic name of the compound shown below. Make sure to include the E or Z designator if necessary. h3c 8 swiggs to ch3 with line to h3c from fifth dip and lin outside 6th

(E).............4.................ethyl................3...................no...................nene

Provide the systematic name of the compound shown below. Make sure to include the E or Z designator if necessary. h3c 8 swiggs to ch3 with line to f from third dip with line inside third

(Z)...................4...................fluoro...................3................heptene

Name the structure. o double to c top to h bottom to c bottom to hoch2 c double to c top to c triple to ch and c line down to ch2ch4

(Z)...............3..................ethyl....................2...................hydroxy.......................methyl.......................2...............penten......................4..................ynal

Draw and name the six alkenes which have the molecular formula C5H10.

-draw 4 swiggles................ with one line under first............... name it................ 1 pentane -draw 4 swiggles............. with one line second swig name it ..............trans .............2 pentene -draw one line down ......................and 3 swig lines going down ..................then one line inside first swig................ name it cis ................2................ pentene -draw 3 swiggs start up ...................with one line under first swig .........................and one line on second dip name it................. 3 methyl...................... 1 butene -draw 3 swigs....................... start up ..................with one line under first swig.................... and straight line up from first dip ..................name it 2.............. methyl............. 1 ...............butene -draw 3 swiggs start up......................... with on line in second swig ...........................and one straight line up from first dip....................... name it 2................... methyl 2........................ butene

β-Phellandrene is a hydrocarbon component of eucalyptus oil whose molecular formula is A molecule of β-phellandrene contains 2 π-bonds. How many rings are in β-phellandrene?

1

Give the product for the reaction that occurs when 1-pentene is treated with Cl2.

1.....................2...................di..................chloro................pentane

Provide an acceptable name for the following compound. hexane ......with 2lines out to br...... and one stick inside

1.......comma.......6......dash......di......bromo......cyclo......hexene

How many carbons are in the planar double-bond system of 3-methylcyclopentene?

2

Which of the following is capable of exhibiting cis-trans isomerism?

2..........................butene

Which of the following compounds will react most rapidly with HCl?

2......................methyl......................2...................hexene

What is the name of the major organic product of the following reaction? ch2 ........................double .................chc .............per ch3 per 3 ........................with an arrow h plus ....................and h20 on top

2...................3..................di................methyl..................2......................butanol

Give the product for the reaction of 1-butene with methanol in the presence of acid.

2...................meth.................oxy...................butane

Provide the systematic name of the alkene below. start up 6 swiggs and double from forth dip

2................ethyl.............1........................hexene

What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?

2.............methyl..............2................penta..................nol

Name the structure ch3...............attached to ch2............. attached to c .............attached to ch2........... attached to ch2........ attached to ch3 ..........with ch 2 attached down to c

2.........dash.........ethyl..........dash.........1.........dash........pentene

What is the IUPAC name for the following compound?ch2 double to c single to ch3 with single down from c to ch2 single to ch3

2......dash.....methly......1......butene

Name the structure ch2 double attached chch2c double to ch2 with single line down to ch3

2......methyl......dash......1......comma......4......dash......penta......diene

Provide an acceptable name for the following compound. 5 swiggle ..........3 line fork on right.......... double stick second dip

2....ethyl....5....coma....5....di....methyl...dash....1dash....hexene

Which of the following carbocations is likely to rearrange?

3 and 4

Draw the structure of two alkenes with molecular formula C4H8 that do not exhibit cis-trans isomerism.

3 swiggle................... going up with ....................first being a......................... double line................. and.................. peace sign....................... with double.................... line up

Upon hydrogenation, which of the following alkenes releases the least heat per mole?

3...................4.....................di....................methyl..............3.....................hexene

A hydrocarbon with molecular formula C20H34 has what degree of substitution?

4

Give the degree of unsaturation for benzene

4

Which of the following is the most stable carbocation?

4

Name the structure. a hexene with cl attached to bottom left line inside bottom right

4.......chloro.......cyclo.......hep.......tene

What is the IUPAC name for the following compound? hexene with ch3 line bottom left and line in next to right line

4.......methyl.......cyclo........hexene

Muscalure, the sex attractant of the common housefly, is an acyclic alkene that contains 23 carbons. How many hydrogen atoms are in a molecule of muscalure?

46

Provide an acceptable name of the compound below. pentagon with 4 line left one right

5...................isobutyl............1................methyl...............cyclo......................pentene

Provide the proper IUPAC name for the alkene shown below. hexane with br top ch3 to right line inside right line

6............bromo..............1..........methyl..........cyclo..........hexene

Name the structure. saw horse ch2ch2ch2cl is on the top right ch3 on bottom right ch3ch2 on top left and ch3ch2 bottom left c double to c in middle

7......dash......chloro......3-ethyl......-4-......methyl-......3-heptene

Which statement(s) are true according to the Hammond postulate?

A and D In an exergonic reaction, the transition state is more similar in energy to the reactant than the product. and In an endergonic reaction, the transition state is more similar in energy to the product than the reactant.

Identify the true statements in the mechanism in the addition of water to an alkene

All of the above

Identify the products of cis-3-methyl-3-hexene with hydrogen bromide.

All of the above answers

Which statement is true in the hydroboration-oxidation of an alkene?

Anti-Markovnikov orientation and syn addition occur.

What is the molecular formula of the hydrocarbon that contains 5 carbon atoms, one ring, and one π bond?

C.....5....H....8

What is the molecular formula of the hydrocarbon that contains 8 carbon atoms, one ring, and two π bonds?

C....8....H....12

Give the general formula for a cyclic alkene.

C....n....H....2....n...dash....2

Which of the following is not an electrophile?

CH2..........................CH2

Which of the following is an allylic alcohol?

CH3CH...........double..............CH..........CH2...........O..........H

Provide the IUPAC name for the alkene shown below. saw horse ch3 top left ch3ch2 bottom left ch2ch2ch3 top right ch 3 bottom right c double c in middle

E.......................3...........................comma...................4...................di..........methyl3............heptene

Which of the following is not a nucleophile?

Fe.....................Br...................3

Identify the most stable carbocation.

Hexagon .......................with a plus inside top dip ......................and a line up that dip to ch2..............ch3

) Which statement is true in the oxymercuration-reduction of an alkene?

Markovnikov orientation and anti addition occur.

Under what conditions is ΔG° equal to ΔH° for a chemical reaction?

Since ΔG° = ΔH° - TΔS°, then ΔG° is equal to ΔH° when TΔS° is zero.

Which of the following statements about ethene, C2H4, is incorrect?

The H-C-H bond angles are approximately 109.5°.

What is the free energy of activation of a one-step reaction? How is it qualitatively related to the rate constant of the reaction?

The free energy of activation of a one-step reaction is the difference in free energy between the transition state and the reactants. As the free energy of activation increases, the rate constant decreases.

Why do reactions tend to proceed at a faster rate as T increases?

The number of molecular collisions that possesses sufficient energy to overcome the barrier to reaction increases.

According to the Hammond Postulate, which of the following is correct?

The transition state of an exothermic reaction step will be more reactant-like than product-like.

Which of the following statements about propene, CH3CHCH2, is correct?

There is a total of eight sigma bonds.

Which of the following correctly describes intermediates and/or transition states?

Transition states have partially formed bonds whereas intermediates have fully formed bonds.

Assign the E or Z configurational label to the following molecule: saw horse in lines only with Br low left

Z

Give the intermediate for the halohydrin reaction.

a halonium ion

.Which of the following contributes to make ΔG° more negative?

a more positive ΔS°

What is the product of the hydrogenation of an alkene?

alkane

) Which of the following alkenes yield(s) 3-bromo-3-methylpentane as the major product upon addition of HBr?

all of them

Name the structure. h2c........double bond......ch.......ch2......I

allyl.........iodide

Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclopentane as the major organic product.

both pentagons first ................................with a line inside right .................................and line out right top........................other with double........................ line from top right

Draw vinyl bromide

ch2 ...........double bond.........ch........br

Give the mechanism for the following reaction. ch3ch double bond ch2 plus h to cl

ch2..................ch...............double................ch2 ...............plus...................h............single................cl........arrow from bond to h..............arrow from single to cl...................big arrow......................c.h2................ch........pos...........single............ch2..............arrow from ch to cl..................big arrow.................ch2...........ch............ch3....line from middle c to cl

Which of the following is vinyl chloride?

ch2..........double........ch..........cl

Which of the following alkenes reacts with HCl at the slowest rate?

ch3...............ch................ch ..................to double bond.................. to ch2 .....................with line from 2nd c .....................down to ch3

Draw all the possible constitutional isomers of C4H8.

ch3...............ch2............ch............... double bond ...............ch2 and ch3..............ch3................ double bond............... ch..............ch3 and ch3c ....................double bond................... ch2................ with c............................ up to ch3 and a square............... and .....................a triangle ..................with ch3......................... out right......................... low corner

Draw the curved arrows to show how CH3CH=CHCH3 reacts with HBr to form a carbocation.

chh3.................ch..................double.................ch.................ch3,,,,,,,,,,,,,plus..............h............br................arrow from bond to h......................arrow from h to br...................big arrow to..................c.h3....................ch2...........plus.............ch............ch3...........plus...................br neg

Draw the product. saw horse starting from right to left h to ch2ch3 to ch3 to h3c

draw a big plus ......................with c in the middle................ then from left to right............... ch3.................ch2...........to............ ch2..............ch3 .....................to ch3............................ to cl

Draw the product. saw horse with starting from left to right h to ch2ch3 to ch3 to h3c and an arrow with h2o on top an h plus on bottom

draw a cross .......................with c in the middle ........................starting from left to right ch3..............ch2 to ch2..................ch3 to .....................ch3 ...................to o...................h

Draw the product. saw horse starting left to right h to ch2ch3 to ch3 to h3c and an arrow with ch3oh on top and h plus at bottom

draw a cross with c in the middle......................... from left to right..................... ch3...................ch2 ................to ch2....................ch3 ...................to ch3 ....................to o...................ch3

Draw the major organic product generated in the reaction below. pentagon with lie to ch3 and arroqw with one hg(OAc)2and h20 on top and nabh4 on bottom

draw a hex................... with a v line on right top side .................to going to o.....................h......................... and left to ch3

Provide the structure of the major organic product in the reaction below. hexagon with double line on top right and an arrow with h i on top

draw a hexagon................. with a v line on right...................... left line with i .....................on left and ch3 on right

Draw the major organic product generated in the reaction below hexagon with a line inside on right and a line out from top right to ch3 and an arrow with h plus and h20

draw a hexagon................... with a v line on top right corner .....................top line to o..............h............................. and bottom to ch3

Draw the major organic product generated in the reaction below. hexagon wth double line on top right corner

draw a hexagon.......................... with a v line ........................on top right .....................with top line to br

Draw the major organic product generated in the reaction below. hexagon with line on top right to ch3 and line inside right side line

draw a hexagon........................... with a v line on right top ..........................with ch3 on top ......................and cl on bottom

Draw the major organic product generated in the reaction below. looks like a stick horse with an arrow with hcl on top

draw a saw horse slanted side ways........................ with a stick in the middle ..............................on right side ..................................top line .................................on right is cl

Provide the major organic product(s) in the reaction below. m shaped with double line in first swig and a two swig line in middle and h.i on arrow

draw an m shape .........................then a v in middle ...............................with an i on right............................... then a straight line down .........................from left side v

Provide the structure of the major organic product of the following reaction. n shape with line up from first dip and an arrow with h plus and h20 on it

draw an n.................. with a v line on top dip................... and o..................h on right

Provide the structure of the major organic product in the reaction below.upside down m with double lines in the middle and an arrow with h2o and h plus on it

draw an upside down m........................ with a v line in the middle ....................and o..................h on right

Provide the major organic product(s) in the reaction below. m shape .........................with l in middle ...................arrow has ch3oh ..................on top ....................and h2so4 in bottom

draw m shape ...................with v line down to h3co .......................on left add straight line on right

Provide the structure of the major organic product of the following reaction. n shape with double line in middle dip up and arrow with h plus and ch3oh on top

draw n shape................. with v line on top dip .....................and o...................ch3 ...................on right

Draw the major organic product generated in the reaction below. m shaped with double lined on first set and one line don in second dip. and an arrow with hbr on top

draw same ......................m shape .............................with a upside down v ............................with br on left line

Draw the major organic product generated in the reaction below. a hexagon with a line from top right then double line down and an arrow with h.c.l on top

draw same as problem.............................. but take double line................................... and make single and double line................................ up to c.............l

Complete the following reaction and provide a detailed, step-by-step mechanism for the process. saw horse missing low right line with hbr on arrow

draw saw hours missing right lower.....................plus...........h.......minus...........br..........arrow from double to h...................arrow from h to br...........big arrow,,,,,,,,,,,,,,,,,sam horse single.............plus................br........arrow from br to single................big arrow.................sam hours with extr line in middle on left

Draw the major organic product generated in the reaction below. up 4 swiggle line with single line under first with arrow that has hcl on top

draw starting up 4 swiggle lines............................... with one line up from first dip................................. to cl

Provide the structure of the major organic product in the reaction below. h3c going down.............. 7 swiggles............... to ch3............... with 3 swiggles ..................up from fourth dip.................. to ch3................. and an arrow.................... with hbr on top

draw the same 7 swiggle line...................... h3c ...................to ch3 .......................with 3 swiggle up from 4th dip............................. to ch3 .......................and on small line .....................from same dip ........................to the right to Br

The Arrhenius equation models how the rate constant k ________.

increases most when Ea decreases and T increases

What is the common name for the following compound?ch3 single bond to c double to ch2 with single bond from c to ch3

isobutylene

Give the major organic product of the reaction shown. saw horse ..................with h.............. to h .................to h ....................to c........................... connected to cross.................. with h3c................ to ch3............. to ch3 .....................and arrow with hbr on top

it has ch3.................... first in .............to bottom and br

Draw the major organic product generated in the reaction below. m line with double line on first and an arrow with h plus and h20

m shape ..........................with one line up first dip .................to o................h

Provide the major organic product(s) in the reaction below. m shape arrow with h20 on top and h2so4 on bottom

m shape .........................with v line down.................right going to o...............h .............................and left add line down)

Draw the major organic product generated in the reaction below. m shape with double line on first line and on line down in the middle with an arrow with h plus and h2o

m shape........................ with a v shape ....................and o.....................h...................... on right stick

Draw the major organic product generated in the reaction below. n shape with linr down sec dip arrow contains Hg

n shape ...................with one line down one up .............................going to o...................h

Which of the following best describes the geometry about the carbon-carbon double bond in the alkene below? saw horse c double bond c from left to right ch3, c1,cl,ch3

neither

Identify the nucleophiles and electrophiles. -OH, BH3, H2O, +CH3, NH3, Br-

nucleo............philes:.............. -OH,.............. H2O,........... NH3,..............Br- electro..............philes:.................. BH3,................ +CH3

What is the major product of the following reaction?

number 3 has ch3 and oh on top right

Draw (E)-2-methyl-3-hexen-1-ol.

o..............h line up................... then swigg to left................... 4 times line down line up from first dip and side line on 3rd swigg

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

oxy..............mer.................curation.................de...................mer............curation

Draw the structure of (Z)-4-ethyl-3,6-dimethyl-3-heptene.

saw horse ..................... left top straight line .................lower and upper right straight lines................... then a v line on right top straight line

Draw the structure of (Z)-4-ethyl-3-methylheptene.

saw horse .........................add line to top left ....................iadd line to top right...................and one line up................one line side from lower right side

Which alkene reacts the fastest with HBr?

saw horse .....................with both h3c on left ......................and both h on the right

Draw the structure of (Z)................1............chloro..............2.............methyl............2..................butene.

saw horse................... top left clh3c .....................bottom left h3c .....................top right ch3 ........................bottom left h.......................... double in middle

Give the hybridization, shape, and bond angle for a carbon in ethene

sp2, trigonal planar, 120°

Draw the structure of propyl vinyl ether

start up 5 swiggs........................... last one is double............................ and a circle .....................on dip 3

For an endergonic reaction step, the Hammond postulate allows one to say that ________.

the transition state of the step resembles the products of the step

Name the structure. saw horse cith ch3ch2 top left hoch2 bottom left c triple ch top right and ch2ch6 bottom right

trans-2,3-diethylpent-2-en-4-yn-1-ol

Name the structure. saw horse with ch3 top left ch3ch2 bottom left ch2ch2ch2oh on top right and ch3 bottom right

trans...................4...............5..............di............methyl...............4.....................hepten..............1................o...........l

Give the possibilities in structure for a compound with a formula of C6H10.

two rings, two double bonds, one double bond + one ring, or one triple bond

Provide the structure of the major organic product in the reaction below upside down m shape with double lines in middle and arrow with ch3ch2oh on top and h2s04 bottom

upside down m............................... with v line in middle ..........................on right is O.............................. wth a sith v connected to it

Which of the following correctly describes the reaction shown?

ΔH° <0 and ΔS <0