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Download E midterm Organic chemistry 1 (Chem-40010) (fall) University of California (San Diego) and more Exams Organic Chemistry in PDF only on Docsity!
ar bet bah tore f hawt wd pea [> Question 1 Identify the most plausible mechanism for the ACID-BASE reaction below: ———_+ 5 ei :O: hae 7: —™~ vA . PRES ac) \ #3 AS + Hos ©. oH z@: Asn Ox ge? ae XH oo H D Question 2 Determine the position of equilibrium for the ACID-BASE reaction below: 5 OH same 2 hes ae ae ©: 6H less stable | * more stable cannot react - ©. on a vhs. more stable = Vi. 2 ee ‘OH + OH a] less stable [> Question 4 Determine the position of equilibrium for the ACID-BASE reaction below: | SA + Or | “a Ot : S + O:-~N” “NZ : Sa \ A Loo): cannot react Cr™ o* Co uN LAS Se -4 o+ 3 “NS S a SS + wf Gite less stable ~~ 2 more stable / ‘\ a’ . ee ee / VAL Cc: Us —— S69 + Nite same same , °. / ' D: SS ) cc accra (igh — + oN H) more stable oC] less stable > | Question 5 ae " Propose a chemical structure for the name below. Make sure to clearly define the stereochemistry where applicable: 2-chloro-3-ethy!-2,4-difluoro-4-methylnonane | A B c D At QO OE Oe OA i OB oc @D | Au 4 Question 7 Propose a chemical structure for the name below. Make sure to clearly define the stereochemistry where applicable: (Z)-2-bromo-1-chloro-1 -fluoroprop-1-ene A B Cc D E Br cl F Cl Br Cl CH3 H3C Cl H3C Br Bn CH3 F Br OA OB @c OD ) | Question 8 Propose a chemical structure for the name below. Make sure to clearly define the stereochemistry where applicable: (1R,3R)-3-methylcyclohexan-1-ol A B Cc D -Q Q Q Q | Question 10 Identify how many C (CARBON) atoms have sp? hybridization for the compound below: A 5 (five) sp* C atoms OA OB @ a) O ie) Bi Cc 6 (six) _ 7 (seven) sp* C atoms '- sp? C atoms D 8 (eight) sp* C atoms Question 11 Identify how many C (CARBON) atoms have sp” hybridization for the compound below: A 5 (five) sp? C atoms OA OB @c B Cc 6 (six) 7 (seven) sp? C atoms sp* C atoms D 8 (eight) sp? C atoms 0.5 pts Question 13 Ve 0.5 Identify the type of hybridization (sp, sp?, sp3) for all N (NITROGEN) atoms of the following compound: A B Cc D 4(one)sp°Natom O(zero)sp*Natom 1(one)sp*Natom 2 (two) sp? N atom 4(one)sp?Natom 2(two)sp?Natom 2(two)sp?Natom 0 (zero) sp? N atom 1 (one) sp N atom 1 (one) sp N atom O(zero)spNatom 1 (one) sp N atom Question 14 Identify how many N (NITROGEN) atoms have sp? hybridization for the compound below: A 1 (one) sp* N atoms a ® ~ UN | HN ati GB c 2 (two) 3 (three) sp* N atoms sp? N atoms D 4 (four) sp? N atoms > Question 16 Identify how many N (NITROGEN) atoms have sp hybridization for the compound below: | : ® ~N UN | HN J A B Cc D 1 (one) 2 (two) r 3 (three) 4 (four) sp N atoms sp.N atoms sp N atoms sp N atoms Oo 0 © fa) wo > C Oo Question 17 Identify the type of hybridization (sp, sp?, sp?) for all C (CARBON) atoms of the following compound: N | N: ® N , N I HN A B. Cc 9 (nine) sp* C atom 41 (eleven) sp? C atom 10 (ten) sp” C atom 41 (eleven) sp* C atom 42 (twelve) sp?C atom 11 (eleven) sp? atom 11 (eleven) sp*C atom 10 (ten) sp? C atom 4 (one) sp C atom 0 (zero) sp C atom 1{one) sp C atom 1 (one) sp C atom AQUCSUUT AZ For the compound below please choose the correct set of. chair and flipped chair conformations: B (1R,2S)-1,2-dimethylcyclohexane CH3 ( ) Lh CH, rl CH3 CH; vi CH, palace —— | | CH3 NEL. ci, ee CH3 ~ CH3 ; CH, Ye CH; eee [> Question 20 For the compound below please choose the correct set of-chair and flipped chair conformations: (1R,3R)-1,3-dimethylcyclohexane CH; : “~CH A LIF SS oma eas we CH, CHs CH, B aie ee yeee ae CH; c La cere EE sD a il H3C : CH, Dp LPs a oa CH. CH; 
