Exam+4+Key - Chemistry 2311 Name EXA M<5 Z SpringI 2009...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chemistry 2311 Name EXA M [<5 Z SpringI 2009 Exam 4- Chapters '7 and 8 (1) Draw the major organic product for each of the following reactions. Be sure to designate the regiochemistry and stereochemistry when appropriate. [3 Fig Q Pedal [8) H V CH(CH3)2 CH3CH20h Na H3O CI ——> CH3CH20H H H CH3 (b) H3C\ £31.13 3“ CH3 85% H3PO4 (:C—C" ———> U H § \ fl H0 CH3 (C) H2 C ..——_..- /C/ \CHs (1)Li,CH3CH2NH2,-78°C H\ / / H3C\ /c/ ——-—> fh E2 (2) NH4C| (d) H30 \CH3 \ (CH3)3CO K+ chf /0\ /CH3 \ B c r I (CH3)3COH H ’H (e) Cl C( CI ,ccr : __..2_4_>. “| + Hscllllllu H30 Hie . H30. (0 0H 5H (1) 8H3. THF CH - (“H3 CH3 ——>- “ 3 + (2) H202, NaOH (1;) 02H5 H \ / CH2I2, Zn(Cu) ' /C=c\ ——+ E'E/I“ : :3H + H; \‘..E‘b H CH3 ‘H Me. M: H (h) “2 ICI H CH 30\C/°\C/ 2 ~—-» H2 H ' I _ Cl [1) “30 OH \C—HC-lfi‘st H2804 0 How" \ "h—ab J H39 CH3 U] B (1 I) r moe H3C—CEC—CH2 2 5“ \ 0 CH3 CCI4, 0 C /—\ [k] Br H3C\C/E\ HBr \i H2 CH2 (1) 6r 3! C H3 3 0H E5 (2] Draw the structures for the products in each of the reactions in the following sequence. Cfikc H30\ §9H3 (1) 03. CHZCIZ. —78°C 6' CH "‘““—" —+ CHZO / 2 H30/ \c/ (2) ZnIHOAc | CH3 (1) NaNHz, liq. NH3 3 equivalents Cl C] (2) CHaBr 3 1 mole H2. PdfCaCOa quinoline (‘1) 0804, pyridine (2) NaHSO3, H20 HO OH \ / HHHI“.C—-C-IIII”|H / (H3C)3C CH3 (3) Draw a valid mechanism for each of the following reactions. El H H Br H H Br \ / Br2.CC|4 \ ,“MCH3 + HSCMH‘ / C—_C -——+ .C—C" "0—0., \\“‘\ "II H3C/ \CH3 H3C H] \Br 8/ \H ’CH3 H .H ‘ q; I \ Br? CH B\/\ H CH CH4 )cfia "‘——’ “3°on 3 /_> owl m 3 _ . M H H H5 H Bf ‘Br'fifl L7 'Br (9 Hscfcé BY; ~\(,l’l3 I" \ a (b) "gr" [:2- Pfi'j H CH<CH3)2 CH3CH20'Na’“ H3O —-—l- H CH30H20H H Cl CHBCHZCfl/D H H3C MK / H H Cc. [bl 9+1] (9 j (c) ethyne (acetylene) to mesa-2,3~dibromobutane [4] How would you carry out the following transformations. You may use any organic and/or inorganic reagents. (a) Cyclohexanol to cis-1,2-cyclohexanediol Br l tBu (PKG) QJY M 8 Br: 6 meso H—E—H ———9 r . r 8( : “a H—Eze H. / H3c/ H -E-—— H 99‘ H 3&NQN/fz ' ‘6' m3) -—- CH Br v eat—CH3 -—L—> CH5————-——c: H5 E; 15 gal-15] How would you chemically distinguish between each of the following? P (a) trans-Z-hexene and cyclohexane AWO 1* Add Br; and look ¥or change in color with at.ch and no color cllSothearahcg {er alkounc. (b) 1-butyne and 1-butene 4AM * Oxumercurod-ion /Demarcuvod1'0h ——~9 alkym uces oi ltd—one CUnd alkene PmducQS om qlcolnol [c] 1-hexyne and 2-hexyne 6M \ \ 9e Adding NqMHz/flw‘NHs -Fo{lowecl by CHBB, will am, a {on er chm ail-91nd} afkgnfi 14% Hit first and no TECLCHW r Hm: second. [i Pis caucle Indicate true (T) or false (F) for each of the following statements. T (a) trans-Z—butene is thermodynamically more stable than cis-Z—butene but cis- cyclooctene is thermodynamically more stable than trans—cyclooctene. T [b] The preferential formation of one product, because the free energy of activation leading to its formation is lower than that for another product, is termed kinetic control. F (c) The tert-butyl cation is a Lewis base. [(1] A carbocation is an intermediate in the E2 reaction mechanism. F (e) When trans—l-bromo-2-methy1cyclohexane is reacted with sodium ethoxide in ethanol, the major product is l-methylcyclohexene. T [f] Alcohols can be both acids and bases. F [g] The 2-butyl cation is more stable than the 2-methyl-2-propyl cation. "'1' (h) Ethanol is a stronger acid than 1-butyne. T [i] A vicinal dihalide has halogen atoms on adjacent carbon atoms. F (j) Reaction of l-butene with borane followed by sodium borohyride leads to the formation of 1,2-butanedio]. ...
View Full Document

This note was uploaded on 02/22/2012 for the course CHBE 2300 taught by Professor Kawajiri during the Spring '08 term at Georgia Tech.

Page1 / 6

Exam+4+Key - Chemistry 2311 Name EXA M<5 Z SpringI 2009...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online