(1) Draw the major organic product for each of the following reactions. Be sure to designate the...

Question

(1) Draw the major organic product for each of the following reactions. Be sure to designate the regiochemistry and stereochemistry when appropriate. (a) (b) (c) (d) (e) (f) (g) (h) (i) (j) (k) (l) (m) (n) (o) (2) Draw the structures for the products in each of the reactions in the following sequence. (3) Draw a reasonable mechanism for each of the following reactions. (b) CH(CH3)2 Cl H H H H3C CH3CH2O - Na + CH3CH2OH H3C H H CH(CH XXXXXXXXXXHow would you carry out the following transformations. You may use any organic and/or inorganic reagents. (a) cyclohexanol to trans-1,2-cyclohexanediol (b) 1-pentanol to 2-bromopentane (c) ethyne (acetylene) to meso-2,3-dichlorobutane (5) How would you chemically distinguish between each of the following? (a) cis-2-pentene and cyclopentane (b) 1-propyne and propane (c) 1-hexyne and 2-hexyne (6)Indicate true (T) or false (F) for each of the following statements. (a) trans-2-butene is thermodynamically more stable than cis-2-butene but cis-cyclooctene is thermodynamically more stable than trans-cyclooctene. (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. (c) The tert-butyl carbonium is an electrophilic species. (d) A carbocation is an intermediate in the E2 reaction mechanism. (e) When trans-1-bromo-1-methylcyclohexane is reacted with potassium tert-butoxide in ethanol, the major product is 1-methylcyclohexene. (f) Acetic acid can be an acid or a base. (g) The 2-butyl cation is more stable than the 2-methyl-2-propyl cation. (h) Ethanol is a stronger acid than 1-butyne. (i) A geminal dihalide has halogen atoms on adjacent carbon atoms. (j) Reaction of 1-butene with borane in tetrahydrofuran followed by reaction with sodium borohyride and sodium hydroxide leads to the formation of 1,2-butanediol. (k) The heterogeneous addition of hydrogen (H2 + Pt) to 2-butyne results in the preferential formation of trans-2-butene. (l) In general, eliminations reactions are favored over competing substitution reactions at lower temperatures.

David · Accepted Answer

Organic Chemistry Test Paper- Solutions 
Question #1 
Question a  
Answer 
It is an elimination reaction. E1 elimination happens. First a secondary carbocation forms. It 
rearranges by 1,2 methyl  shift to form a tertiary carbocation. It  undergoes deprotonation to form 
2,3-dimethylbutane, which is a stable alkene due to hyper conjugation.
Question b 
Answer 
Internal alkynes are reduced by Li in presence of ethanamine to form trans alkenes. It is due to the 
trans addition of the H atom to the alkene. The H atoms are generated from the reaction of Li and 
amine. It happens at low temperature- 78C
Question c 
This question also involve an elimination reaction. Cl goes first to form a carbocation, which undergo 
two rearrangements to form a tertiary carbocation. That 3o carbocation undergo deprotonation to 
form an alkene. The reaction  is represented below. 
carbocation  rearragement
deprotonation
 
Question d 
This is an addition reaction. First the Cl+ from Cl2 takes the double bond to form a cyclic chloronium 
ion. Then, the Cl- attacks this bridged intermediate from backside to form a trans dichloro product.
Question e 
This reaction is addition of water to form an alcholol. Addition happens by anti Markonikoff’s rule. 
The reaction is hydroboration, oxidation. 
hydroboration- oxidation
 
Question f 
This is again an elimination process. Bimolecular E2 elimination happens 
E2 elimination
 
Question g 
Here,

(1) Draw the major organic product for each of the following reactions. Be sure to designate the regiochemistry and stereochemistry when appropriate. (a) (b) (c) (d) (e) (f) (g) (h) (i) (j) (k) (l)...

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