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DAT Bootcamp - Reaction Summary Sheet 100%

DAT Organic Chemistry Reaction Summary Sheet Alkene Reactions Hydrohalogenation Hydrohalogenation (with Rearrangement) Halogenation Hydrobromination with Peroxide Hydration Hydration (with Rearrangement) Bromination in H2O OxymercurationDemurcuration HydroborationOxidation Syn-Hydroxylation Syn-Hydroxylation Anti-Hydroxylation Addition of an Alcohol Bromination in Alcohol AlkoxymercurationDemurcuration Epoxidation www.datbootcamp.com 1 of 26|Page Catalytic Hydrogenation Ozonolysis (Reducing Conditions) Ozonolysis (Oxidizing Conditions) Oxidative Cleavage Alkyne Reactions Catalytic Hydrogenation (Catalytic Reduction) Reduction to CisAlkene Reduction to TransAlkene Hydrohalogenation with HBr (Terminal Alkyne) Hydrohalogenation with HBr (Internal Alkyne) Halogenation with Br2 Hydration of an Internal Alkyne Hydration of a Terminal Alkyne (Markovnikov) Hydration of a Terminal Alkyne (Anti-Markovnikov) SN2 Addition of an Acetylide Ion to an Alkyl Halide SN2 Addition of an Acetylide Ion to a Ketone SN2 Addition of an Acetylide Ion to an Epoxide www.datbootcamp.com 2 of 26|Page Ozonolysis Oxidative Cleavage www.datbootcamp.com 3 of 26|Page Free Radical Halogenation Reactions Free Radical Halogenation using Bromine (more selective) Free Radical Halogenation using Chlorine (less selective) Br Br2 hv or Δ Cl Cl Cl2 Cl hv or Δ Cl Allylic/Benzylic Bromination NBS hv or Δ or ROOR Br NBS hv or Δ or ROOR Br Br Diels Alder Reactions Diene Addition to a Dienophile (Alkene) hv or Diene Addition to a Dienophile (Alkyne) hv or Diene Addition to a cis Dienophile hv or same Diene Addition to a trans Dienophile hv or enantiomers Diene Addition to a substituted Dienophile H O hv or H endo (Major) O O H H H H www.datbootcamp.com O H O exo (Minor) H 4 of 26|Page Grignard Reactions Addition of a Grignard Reagent to an Aldehyde O 1.

https://www.pdf-archive.com/2018/06/19/dat-bootcamp---reaction-summary-sheet/

19/06/2018 www.pdf-archive.com

idaf 93%

Elektronische Spionage ● ● ● Elektronisches Kommunikationsgerät -- besonders dein Handy -- kann verwendet werden um dich zu spionieren NICHT NUR können alle diene Nachrichten (Stimme, Text, Video, u.s.w.) abgefangen werden Sondern auch (ACHTUNG!) kann dein eigenes elektronisches Geräte als Spionagezeug gegen dich selbst verwendet werden, wenn du es nicht benutzest (auch wenn du denkst dein Gerät ausgeschaltet ist!!) Spezifische Elektronische Spionage ● Diene Textnachrichten (SMS, Whatsapp, Viber, u.s.w.), und diene Sprachanrufe werden abgefangen und gelesen/gehören ● Deine E-mails werden nicht nur vom gewünschten Empfänger gelesen ● ACHTUNG:

https://www.pdf-archive.com/2015/11/10/idaf/

10/11/2015 www.pdf-archive.com

J Chem Eng Data 55, 2010, 5359-5364 89%

Experimental and G4 Calculated Gas-Phase Standard State (298.15 K, 1.01325 bar) Enthalpies of Formation (∆fH°(g)) for Various Organic Compoundsa ∆fH°(g)/(kJ · mol-1) compound (1R,2R,4R,5R)-tricyclo[3.2.1.02,4]oct-6-ene (E)-hexa-1,5-diyne-3-ene (Z)-3-penten-1-yne (Z)-hexa-1,5-diyne-3-ene 1-buten-3-yne 1-cyclopropylpenta-1,3-diyne 1-propynylbenzene 1,1-dimethylcyclopropane 1,1,1-trichloroethane 1,1,1-trifluoroethane 1,2-bis(methylene)cyclobutane 1,2,3-trichlorobenzene 1,2,4-trichlorobenzene 1,3-cyclopentadiene 1,3-cyclopentadiene, 5-(1-methylethylidene)1,3-dioxol-2-one 1,3,5-triazine 1,3,5-trichlorobenzene 1,3,5-trioxane 1H-imidazole 1H-pyrazole 2-butynedinitrile 2-methyl-1-buten-3-yne 2-methyl-1H-imidazole 2-methylpyridine 2-norbornene 2-propenenitrile 2,2-dimethylbutane 2,3-bis(methylene)bicyclo[2.2.0]hexane 2,3-diazabicyclo[2.2.1]-hept-2-ene 2,3-dihydrothiophene 2,3-dimethylbutane 2,5-norbornadiene 3-(cis-ethylidene)-1-cyclopentene 3-methylene-1,4-cyclohexadiene 3-methylenecyclopentene 3,4-dimethylenecyclobut-1-ene 3,6-bis(methylene)-1,4-cyclohexadiene 4-methylene-2-oxetanone 5,5-dimethyl-1,3-cyclopentadiene 6-methylfulvene 7-methylenebicyclo[2.2.1]-heptane aniline antitricyclo[3.2.0.02,4]hept-6-ene antitricyclo[3.2.0.02,4]heptane antitricyclo[4.1.0.02,4]heptane antitricyclo[4.2.0.02,5]octane benzene benzyne bicyclo[1.1.0]but-1(3)-ene bicyclo[1.1.0]butane-1-carbonitrile bicyclo[2.1.0]pent-2-ene bicyclo[2.1.0]pentane bicyclo[2.1.0]pentane-1-carbonitrile bicyclo[2.1.1]hex-2-ene bicyclo[2.2.0]hex-1(4)-ene bicyclo[2.2.0]hexane bicyclo[3.2.0]hept-1-ene bicyclo[3.2.0]hept-1(5)-ene bicyclo[3.2.0]hepta-2,6-diene bicyclo[3.2.1]octa-2,6-diene expt.

https://www.pdf-archive.com/2015/11/03/j-chem-eng-data-55-2010-5359-5364/

03/11/2015 www.pdf-archive.com

J Chem Engr Data 56, 2011, 350-355 87%

The G4 prediction of 8.32 eV is at the lower formula C4H4 C4H4 C4H4 C3H3N C4H6 C4H6 C3H5N C4H8 C4H8 C4H8 C3H7N C3H7N C3H6O C3H6O C3H6O C2H4O2 C2H2F2 C5H4 C5H4 C5H6 C5H6 C5H6 C5H6 C5H6 C5H6 C4H5N C3O2 C4H4O C3H4N2 C3H4N2 C5H8 C5H8 C4H7N CHF3 C3H6N2 C4H8O C5H12 C5H12 C5H12 C4N2 C6H4 C6H4 C6H4 CS2 C6H6 C6H6 C6H6 C6H6 C2H6OS C4H4N2 C4H4N2 C4H4N2 CAS-RN 689-97-4 2873-50-9 1120-53-2 107-13-1 157-33-5 822-35-5 6788-85-8 115-11-7 590-18-1 624-64-6 1072-44-2 503-29-7 75-56-9 503-30-0 75-56-9 64-19-7 75-38-7 21986-03-8 24442-69-1 1574-40-9 646-05-9 542-92-7 78-80-8 5164-35-2 6746-94-7 109-97-7 504-64-3 110-00-9 288-32-4 288-13-1 185-94-4 157-40-4 109-96-6 75-46-7 1467-79-4 109-99-9 78-78-4 463-82-1 109-66-0 1071-98-3 16668-68-1 16668-67-0 6929-94-8 75-15-0 5291-90-7 71-43-2 5649-95-6 3227-90-5 67-68-5 290-37-9 289-80-5 289-95-2 52.0746 52.0746 52.0746 53.0626 54.0904 54.0904 55.0785 56.1063 56.1063 56.1063 57.0944 57.0944 58.0791 58.0791 58.0791 60.0520 64.0341 64.0853 64.0853 66.1011 66.1011 66.1011 66.1011 66.1011 66.1011 67.0892 68.0309 68.0740 68.0773 68.0773 68.1170 68.1170 69.1051 70.0138 70.0931 72.1057 72.1488 72.1488 72.1488 76.0562 76.0960 76.0960 76.0960 76.141 78.1118 78.1118 78.1118 78.1118 78.133 80.0880 80.0880 80.0880 g · mol-1 MW 1-buten-3-yne 1,2,3-butatriene cyclobutadiene 2-propenenitrile bicyclo[1.1.0]butane cyclobutene 1-azetine 2-methyl-1-propene cis-2-butene trans-2-butene 1-methylaziridine azetidine methyloxirane oxetane propylene oxide acetic acid 1,1-difluoroethene 1,2,3,4-pentatetraene penta-1,4-diyne (Z)-3-penten-1-yne 1-penten-3-yne 1,3-cyclopentadiene 2-methyl-1-buten-3-yne bicyclo[2.1.0]pent-2-ene cyclopropylacetylene pyrrole carbon suboxide furan 1H-imidazole 1H-pyrazole bicyclo[2.1.0]pentane spiropentane 2,5-dihydro-1H-pyrrole trifluoromethane dimethylcyanamide tetrahydrofuran isopentane neopentane pentane 2-butynedinitrile (E)-hexa-1,5-diyne-3-ene (Z)-hexa-1,5-diyne-3-ene hex-3-en-1,5-diyne carbon disulfide 3,4-dimethylenecyclobut-1-ene benzene bicyclo[2.2.0]hexa-2,5-diene tris(methylene)cyclopropane dimethyl sulfoxide pyrazine pyridazine pyrimidine name G4 9.61 9.16 8.06 10.96 8.79 9.47 9.31 9.24 9.14 9.15 8.67 8.32 10.09 9.69 10.24 10.62 10.27 8.77 10.31 9.11 9.00 8.59 9.25 8.15 9.19 8.22 10.66 8.89 8.82 9.28 8.66 9.39 8.08 13.77 9.20 9.42 10.02 10.18 10.21 11.94 9.08 9.11 9.08 10.11 8.80 9.29 8.93 9.08 8.86 9.28 8.70 9.39 expt 9.58 ( 0.02 9.15 to 9.40 8.16 to 9.55 10.91 ( 0.01 8.70 ( 0.01 9.43 ( 0.02 9.30 9.22 ( 0.02 9.11 ( 0.01 9.10 ( 0.01 8.7 8.3 to 9.1 10.22 ( 0.02 9.65 ( 0.01 10.22 ( 0.02 10.65 ( 0.02 10.29 ( 0.0 8.67 10.10 to 10.27 9.11 9.00 ( 0.01 8.57 ( 0.01 9.25 ( 0.02 8.0 8.7 8.207 ( 0.005 10.60 8.88 ( 0.01 8.81 ( 0.01 9.25 to 9.38 8.7 9.26 8.0 13.86 9.0 9.40 ( 0.02 10.32 ( 0.05 e10.30 ( 0.08 10.28 ( 0.10 11.40 to 11.81 9.07 9.10 9.6 10.073 ( 0.005 8.80 9.24378 ( 0.00007 9.0 9.0 9.08 to 9.90 9.00 to 9.36 8.74 ( 0.11 9.33 ( 0.07 AIE/eV 110-54-3 72323-66-1 27041-32-3 59502-33-9 35295-57-9 4513-94-4 121-46-0 3217-87-6 67254-49-3 2422-86-8 278-06-8 765-46-8 22635-78-5 108-88-3 109-06-8 62-53-3 108-95-2 51549-86-1 498-66-8 4125-18-2 51273-50-8 174-73-2 24108-33-6 2721-32-6 75-35-4 156-59-2 156-60-5 75-44-5 116-14-3 1072-20-4 4026-23-7 536-74-3 20380-31-8 33284-11-6 37846-63-2 500-24-3 694-87-1 80339-91-9 68344-46-7 20656-23-9 100-42-5 3227-91-6 35438-35-8 75-72-9 63001-13-8 4096-95-1 102575-26-8 102575-25-7 108-90-7 372-18-9 367-11-3 540-36-3 CAS-RN C6H14 C7H6 C7H6 C7H6 C7H6 C5H4N2 C7H8 C7H8 C7H8 C7H8 C7H8 C7H8 C7H8 C7H8 C6H7N C6H7N C6H6O C7H10 C7H10 C7H10 C7H10 C7H10 C4H5N3 C5H8N2 C2H2Cl2 C2H2Cl2 C2H2Cl2 CCl2O C2F4 C8H6 C8H6 C8H6 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 C8H8 CClF3 C8H10 C8H10 C8H10 C8H10 C6H5Cl C6H4F2 C6H4F2 C6H4F2 formula MW 86.1754 90.1225 90.1225 90.1225 90.1225 92.0987 92.1384 92.1384 92.1384 92.1384 92.1384 92.1384 92.1384 92.1384 93.1265 93.1265 94.1112 94.1543 94.1543 94.1543 94.1543 94.1543 95.1026 96.1304 96.943 96.943 96.943 98.916 100.0150 102.1332 102.1332 102.1332 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.1491 104.459 106.1650 106.1650 106.1650 106.1650 112.557 114.0928 114.0928 114.0928 g · mol-1 Table 2.

https://www.pdf-archive.com/2015/11/06/j-chem-engr-data-56-2011-350-355/

06/11/2015 www.pdf-archive.com

playgnd 2 83%

Rubber Flooring  Tough rubber-flooring made up of 80% black recycled-rubber and 20% colour,EPDM (ethylenepropylene-diene-Monomer (M-class) rubber)granules.

https://www.pdf-archive.com/2014/01/13/playgnd-2/

13/01/2014 www.pdf-archive.com

rubberfloringuk 2 83%

Rubber Flooring Uk Rubber Flooring UK is Leading supplier of Rubber Floor products for the Industrial, Commercial, Public, Sporting and Institutional facilities Rubber Flooring  Tough rubber-flooring made up of 80% black recycled-rubber and 20% colour,EPDM (ethylenepropylene-diene-Monomer (M-class) rubber)granules.

https://www.pdf-archive.com/2014/01/13/rubberfloringuk-2/

13/01/2014 www.pdf-archive.com

playgnd 4 83%

Rubber Flooring • Tough rubber-flooring made up of 80% black recycled-rubber and 20% colour,EPDM (ethylene-propylene-diene-Monomer (M-class) rubber)granules.

https://www.pdf-archive.com/2014/02/12/playgnd-4/

12/02/2014 www.pdf-archive.com

gymmat 2 83%

Rubber Flooring  Tough rubber-flooring made up of 80% black recycled-rubber and 20% colour,EPDM (ethylenepropylene-diene-Monomer (M-class) rubber)granules.

https://www.pdf-archive.com/2014/01/13/gymmat-2/

13/01/2014 www.pdf-archive.com

gymmat 4 83%

Rubber Flooring • Tough rubber-flooring made up of 80% black recycled-rubber and 20% colour,EPDM (ethylene-propylene-diene-Monomer (M-class) rubber)granules.

https://www.pdf-archive.com/2014/02/11/gymmat-4/

11/02/2014 www.pdf-archive.com

Sleepwet 74%

Sleepwet mr. B.W.

https://www.pdf-archive.com/2018/03/21/sleepwet/

21/03/2018 www.pdf-archive.com

POR 118 66%

Parlamento de Navarra.

https://www.pdf-archive.com/2017/03/03/por-118/

03/03/2017 www.pdf-archive.com

0bajo 66%

https://www.pdf-archive.com/2017/12/07/0bajo/

07/12/2017 www.pdf-archive.com

0tenor 66%

https://www.pdf-archive.com/2017/12/07/0tenor/

07/12/2017 www.pdf-archive.com

004-bajo 66%

https://www.pdf-archive.com/2018/04/21/004-bajo/

21/04/2018 www.pdf-archive.com