Problem: (i) Which compound is less soluble in water: (a) CH 3(CH2)4CH2OH or (b) CH3(CH2)3CH2OH? (Choose one; give the letter.) (ii) Which compound is releases less heat when it is burned: (a) CH 3(CH2)4CH3 or (b) (CH3)3CCH2CH3? (Choose one; give the letter.) (iii) Which compound has the higher boiling point: (a) CH 3(CH2)3CH3 or (b) (CH3)2CHCH(CH3)2? (Choose one; give the letter.) (iv) A Lewis base can also be known as (a) an electrophile, (b) a nucleophile, or (c) a spectator ion ? (Choose one; give the letter.) (v) Which one is the most basic: (a) (CH3)3CO− ; (b) CH3CH2O−; or (c) (CH3)2CHO− ? (Choose one; give the letter.) (vi) Which compound is more oxidized: (a) CH3CO2H or (b) HOCH2CH2OH ? (Choose one; give the letter. If they are the same, give both letters.) (vii) Which one is the molecular formula of a neopentyl group: (a) C5H9 ; (b) C5H10; (c) C5H11 ; or (d) C5H12 ? (Choose one; give the letter.) (viii) Which compound is an alcohol that is not miscible with water: (Choose one; give the letter.) (a) CH3CH2OCH3; (b) CH3CH2CH2OH; or (c) CH3CH2CH2CH2OH ? (ix) What type of alkyl group is a 1-methylcyclohexyl group: (a) primary ; (b) secondary ; (c) tertiary ; or (d) quaternary (Choose one; give the letter.)  (x) Which compound is more soluble in water: (i) CH3CH2CH2OH or (ii) CH3CH2CH2Cl? (Choose one; give the letter.)  

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(i) Which compound is less soluble in water: (a) CH 3(CH2)4CH2OH or (b) CH3(CH2)3CH2OH? (Choose one; give the letter.)

(ii) Which compound is releases less heat when it is burned: (a) CH 3(CH2)4CH3 or (b) (CH3)3CCH2CH3? (Choose one; give the letter.)

(iii) Which compound has the higher boiling point: (a) CH 3(CH2)3CH3 or (b) (CH3)2CHCH(CH3)2? (Choose one; give the letter.)

(iv) A Lewis base can also be known as (a) an electrophile, (b) a nucleophile, or (c) a spectator ion ? (Choose one; give the letter.)

(v) Which one is the most basic: (a) (CH3)3CO ; (b) CH3CH2O; or (c) (CH3)2CHO ? (Choose one; give the letter.)

(vi) Which compound is more oxidized: (a) CH3CO2H or (b) HOCH2CH2OH ? (Choose one; give the letter. If they are the same, give both letters.)

(vii) Which one is the molecular formula of a neopentyl group: (a) C5H9 ; (b) C5H10; (c) C5H11 ; or (d) C5H12 ? (Choose one; give the letter.)

(viii) Which compound is an alcohol that is not miscible with water: (Choose one; give the letter.) (a) CH3CH2OCH3; (b) CH3CH2CH2OH; or (c) CH3CH2CH2CH2OH ?

(ix) What type of alkyl group is a 1-methylcyclohexyl group: (a) primary ; (b) secondary ; (c) tertiary ; or (d) quaternary (Choose one; give the letter.) 

(x) Which compound is more soluble in water: (i) CH3CH2CH2OH or (ii) CH3CH2CH2Cl? (Choose one; give the letter.)

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Based on our data, we think this problem is relevant for Professor Wang's class at UCB.